With some [dynamic programming](https://repl.it/@jt3280/1-to-5-game) we can find all possibilities. Without exponents, we can go to exactly 75:

    1: 1 * (2 / (3 + (4 - 5)))
    2: (((4 + 5) - 3) / 2) - 1
    3: 1 * (((4 + 5) - 3) / 2)
    4: (2 + (3 * (5 - 4))) - 1
    5: 1 * (2 + (3 * (5 - 4)))
    6: 1 + (2 + (3 * (5 - 4)))
    7: 1 * (2 + (5 * (4 - 3)))
    8: 1 + (2 + (5 * (4 - 3)))
    9: 1 + (2 * (3 - (4 - 5)))
    10: 1 * (2 * (5 * (4 - 3)))
    11: 1 + (2 * (5 * (4 - 3)))
    12: 1 * (2 * ((4 + 5) - 3))
    13: 1 + (2 * ((4 + 5) - 3))
    14: 1 * (2 * ((3 * 4) - 5))
    15: 1 + (2 * ((3 * 4) - 5))
    16: ((4 + (3 * 5)) - 2) - 1
    17: 1 * ((4 + (3 * 5)) - 2)
    18: 1 + ((4 + (3 * 5)) - 2)
    19: (4 * (5 * (3 - 2))) - 1
    20: 1 * (4 * (5 * (3 - 2)))
    21: (2 * ((3 * 5) - 4)) - 1
    22: 1 * (2 * ((3 * 5) - 4))
    23: 1 + (2 * ((3 * 5) - 4))
    24: ((3 * (4 + 5)) - 2) - 1
    25: 1 * ((3 * (4 + 5)) - 2)
    26: 1 + ((3 * (4 + 5)) - 2)
    27: (4 * ((2 * 5) - 3)) - 1
    28: (2 + (3 * (4 + 5))) - 1
    29: 1 * (2 + (3 * (4 + 5)))
    30: (3 + (4 * (2 + 5))) - 1
    31: 1 * (3 + (4 * (2 + 5)))
    32: 1 + (3 + (4 * (2 + 5)))
    33: 1 * ((5 * (3 + 4)) - 2)
    34: 1 + ((5 * (3 + 4)) - 2)
    35: (3 * (4 * (5 - 2))) - 1
    36: 1 * (3 * (4 * (5 - 2)))
    37: 1 + (3 * (4 * (5 - 2)))
    38: (3 * (5 + (2 * 4))) - 1
    39: 1 * (3 * (5 + (2 * 4)))
    40: 1 + (3 * (5 + (2 * 4)))
    41: 1 + (4 * (2 + (3 + 5)))
    42: 1 * (3 * (4 + (2 * 5)))
    43: 1 + (3 * (4 + (2 * 5)))
    44: (5 * (2 + (3 + 4))) - 1
    45: (2 * (3 + (4 * 5))) - 1
    46: 1 * (2 * (3 + (4 * 5)))
    47: ((2 + 4) * (3 + 5)) - 1
    48: 1 * ((2 + 4) * (3 + 5))
    49: 1 + ((2 + 4) * (3 + 5))
    50: 1 * (5 * ((3 * 4) - 2))
    51: 1 + (5 * ((3 * 4) - 2))
    52: 1 * (4 * ((3 * 5) - 2))
    53: (2 * (3 * (4 + 5))) - 1
    54: 1 * (2 * (3 * (4 + 5)))
    55: 1 + (2 * (3 * (4 + 5)))
    56: 1 + (5 * (3 + (2 * 4)))
    57: ((3 * (4 * 5)) - 2) - 1
    58: 1 * ((3 * (4 * 5)) - 2)
    59: 1 - (2 - (3 * (4 * 5)))
    60: 2 * (3 * (1 + (4 + 5)))
    61: (2 + (3 * (4 * 5))) - 1
    62: 1 * (2 + (3 * (4 * 5)))
    63: 1 + (2 + (3 * (4 * 5)))
    64: 1 * (2 * (4 * (3 + 5)))
    65: 1 + (2 * (4 * (3 + 5)))
    66: 1 * (3 * (2 + (4 * 5)))
    67: 1 + (3 * (2 + (4 * 5)))
    68: 1 * (4 * (2 + (3 * 5)))
    69: (2 * (5 * (3 + 4))) - 1
    70: 1 * (2 * (5 * (3 + 4)))
    71: 1 + (2 * (5 * (3 + 4)))
    72: 2 * (1 + (5 * (3 + 4)))
    73: (3 * (5 * (1 + 4))) - 2
    74: 2 + (3 * (4 * (1 + 5)))
    75: 3 * (5 * ((2 + 4) - 1))

With exponents, we can go to 177:

    76: 1 + (3 * (5 ^ (4 - 2)))
    77: (2 - (5 - (3 ^ 4))) - 1
    78: (4 + (3 * (5 ^ 2))) - 1
    79: 1 * (4 + (3 * (5 ^ 2)))
    80: (((2 ^ 3) - 5) ^ 4) - 1
    81: 1 * (((2 ^ 3) - 5) ^ 4)
    82: 1 + (((2 ^ 3) - 5) ^ 4)
    83: ((5 + (3 ^ 4)) - 2) - 1
    84: 1 * ((5 + (3 ^ 4)) - 2)
    85: 1 + ((5 + (3 ^ 4)) - 2)
    86: (3 * (4 + (5 ^ 2))) - 1
    87: 1 * (3 * (4 + (5 ^ 2)))
    88: 1 + (3 * (4 + (5 ^ 2)))
    89: 1 + (2 + (5 + (3 ^ 4)))
    90: 1 * (3 * (5 * (2 + 4)))
    91: 1 + (3 * (5 * (2 + 4)))
    92: 1 * ((3 * (2 ^ 5)) - 4)
    93: 1 - (4 - (3 * (2 ^ 5)))
    94: (5 * (3 + (2 ^ 4))) - 1
    95: 1 * (5 * (3 + (2 ^ 4)))
    96: ((4 * (5 ^ 2)) - 3) - 1
    97: 1 * ((4 * (5 ^ 2)) - 3)
    98: 1 + ((4 * (5 ^ 2)) - 3)
    99: (4 * (5 * (2 + 3))) - 1
    100: 1 * (4 * (5 * (2 + 3)))
    101: 1 + (4 * (5 * (2 + 3)))
    102: (3 + (4 * (5 ^ 2))) - 1
    103: 1 * (3 + (4 * (5 ^ 2)))
    104: 1 + (3 + (4 * (5 ^ 2)))
    105: ((5 ^ 2) + (3 ^ 4)) - 1
    106: 1 * ((5 ^ 2) + (3 ^ 4))
    107: (3 * (4 + (2 ^ 5))) - 1
    108: 1 / ((3 ^ (2 - 5)) / 4)
    109: 1 + (3 * (4 + (2 ^ 5)))
    110: 1 - ((2 ^ 4) - (5 ^ 3))
    111: (4 * (3 + (5 ^ 2))) - 1
    112: 1 * (4 * (3 + (5 ^ 2)))
    113: 1 + (4 * (3 + (5 ^ 2)))
    114: 1 + ((2 ^ 5) + (3 ^ 4))
    115: (4 * ((2 ^ 5) - 3)) - 1
    116: 1 * (4 * ((2 ^ 5) - 3))
    117: (2 * ((4 ^ 3) - 5)) - 1
    118: (((5 ^ 3) - 4) - 2) - 1
    119: (2 * (3 * (4 * 5))) - 1
    120: 1 * (2 * (3 * (4 * 5)))
    121: 1 + (2 * (3 * (4 * 5)))
    122: (2 - (4 - (5 ^ 3))) - 1
    123: 1 * (2 - (4 - (5 ^ 3)))
    124: 1 - ((4 - (5 ^ 3)) - 2)
    125: 1 * ((4 * (2 ^ 5)) - 3)
    126: ((4 + (5 ^ 3)) - 2) - 1
    127: 1 * ((4 + (5 ^ 3)) - 2)
    128: 1 - (2 - (4 + (5 ^ 3)))
    129: 1 + (2 ^ ((3 * 4) - 5))
    130: (2 + (4 + (5 ^ 3))) - 1
    131: 1 * (2 + (4 + (5 ^ 3)))
    132: 1 + (2 + (4 + (5 ^ 3)))
    133: 1 * (5 + (2 ^ (3 + 4)))
    134: 1 + (5 + (2 ^ (3 + 4)))
    135: 3 * (5 * (1 + (2 * 4)))
    136: 2 * ((5 + (4 ^ 3)) - 1)
    137: (2 * (5 + (4 ^ 3))) - 1
    138: 1 * (2 * (5 + (4 ^ 3)))
    139: 1 + (2 * (5 + (4 ^ 3)))
    140: 1 * (4 * (3 + (2 ^ 5)))
    141: 1 + (4 * (3 + (2 ^ 5)))
    142: 1 + ((2 ^ 4) + (5 ^ 3))
    143: ((3 + (4 + 5)) ^ 2) - 1
    144: 1 * ((3 + (4 + 5)) ^ 2)
    145: 1 + ((3 + (4 + 5)) ^ 2)
    146: (1 + (3 ^ (2 + 4))) / 5
    147: 3 + (4 * ((1 + 5) ^ 2))
    148: (5 + ((3 * 4) ^ 2)) - 1
    149: 1 * (5 + ((3 * 4) ^ 2))
    150: 1 + (5 + ((3 * 4) ^ 2))
    151: (2 * ((3 ^ 4) - 5)) - 1
    152: 1 * (2 * ((3 ^ 4) - 5))
    153: 1 - (2 * (5 - (3 ^ 4)))
    154: 2 * (1 - (5 - (3 ^ 4)))
    155: 5 * (((4 ^ 3) / 2) - 1)
    156: ((2 * (3 ^ 4)) - 5) - 1
    157: 1 * ((2 * (3 ^ 4)) - 5)
    158: 1 - (5 - (2 * (3 ^ 4)))
    159: ((5 * (4 ^ 3)) / 2) - 1
    160: 1 * ((5 * (4 ^ 3)) / 2)
    161: 1 + ((5 * (4 ^ 3)) / 2)
    162: 2 * (3 ^ (4 * (1 ^ 5)))
    163: 3 + (5 * (2 ^ (1 + 4)))
    164: 2 * ((1 ^ 5) + (3 ^ 4))
    165: 5 * (1 + ((4 ^ 3) / 2))
    166: (5 + (2 * (3 ^ 4))) - 1
    167: 1 * (5 + (2 * (3 ^ 4)))
    168: 1 + (5 + (2 * (3 ^ 4)))
    169: (1 + (3 + (4 + 5))) ^ 2
    170: 2 * ((5 + (3 ^ 4)) - 1)
    171: (2 * (5 + (3 ^ 4))) - 1
    172: 1 * (2 * (5 + (3 ^ 4)))
    173: 1 + (2 * (5 + (3 ^ 4)))
    174: ((3 + 4) * (5 ^ 2)) - 1
    175: 1 * ((3 + 4) * (5 ^ 2))
    176: 1 + ((3 + 4) * (5 ^ 2))
    177: 3 * ((4 ^ (1 + 2)) - 5)

Out the first 500 (nonzero) natural numbers, we can make 395. Out of the first 1000, we can make 554.

Bonus: including integer division only takes us a bit further, to 182.

    178: (5 ^ 4) // (3 + (1 / 2))
    179: (4 * (5 * (3 ^ 2))) - 1
    180: ((2 + (5 / 3)) ^ 4) // 1
    181: 1 + (4 * (5 * (3 ^ 2)))
    182: (5 ^ (4 - (1 / 3))) // 2

I added flags for modulo and bitwise and/or/xor too, but those don't extend our reach at all beyond 182. <s>Out of binary operations for now...</s>

Bonus 2: When we add concatenation to the original four + exponentiation, it takes us all the way to 668, and covers 980 of the first 1000 numbers!

    178: 1 || (2 * (3 || (4 + 5)))
    179: 1 || (4 + (3 * (5 ^ 2)))
    180: 1 * (4 * (5 * (3 ^ 2)))
    181: (2 + (4 ^ (5 - 3))) || 1
    182: 1 || ((4 * (5 - 3)) || 2)
    183: 1 || (((2 ^ 5) / 4) || 3)
    184: 1 || (2 * ((4 || 5) - 3))
    185: 1 || ((5 * (3 || 4)) / 2)
    186: 1 || (2 + ((3 + 5) || 4))
    187: 1 || (3 * (2 || (4 + 5)))
    188: 1 || (2 + (5 + (3 ^ 4)))
    189: 1 || (((4 + 5) || 2) - 3)
    190: 1 || (3 * (5 * (2 + 4)))
    191: (2 + ((4 * 5) - 3)) || 1
    192: 1 || ((3 * (2 ^ 5)) - 4)
    193: 1 || (3 + (2 * (4 || 5)))
    194: 1 || ((3 * (5 - 2)) || 4)
    195: 1 || (2 + ((4 + 5) || 3))
    196: 1 || (2 * (3 + (4 || 5)))
    197: 1 || ((4 * (5 ^ 2)) - 3)
    198: (((4 * 5) || 2) - 3) - 1
    199: 1 || (((2 * 5) || 3) - 4)
    200: (((4 * 5) || 3) - 2) - 1
    201: (2 + ((5 || 4) / 3)) || 1
    202: 1 + (((4 * 5) || 3) - 2)
    203: (4 * ((5 || 3) - 2)) - 1
    204: 1 * (4 * ((5 || 3) - 2))
    205: 1 + (4 * ((5 || 3) - 2))
    206: ((5 * (4 || 2)) - 3) - 1
    207: 1 * ((5 * (4 || 2)) - 3)
    208: ((2 + (5 ^ 4)) / 3) - 1
    209: 1 * ((2 + (5 ^ 4)) / 3)
    210: (2 || ((3 * 5) - 4)) - 1
    211: (2 || ((5 - 4) ^ 3)) || 1
    212: 1 + (2 || ((3 * 5) - 4))
    213: 1 * (2 || ((5 - 4) || 3))
    214: 1 + (2 || ((5 - 4) || 3))
    215: (2 || (4 ^ (5 - 3))) - 1
    216: 1 * (2 || (4 ^ (5 - 3)))
    217: 1 + (2 || (4 ^ (5 - 3)))
    218: (2 || (4 + (3 * 5))) - 1
    219: 1 * (2 || (4 + (3 * 5)))
    220: (((3 * 5) ^ 2) - 4) - 1
    221: (2 || (3 + (4 - 5))) || 1
    222: 1 - (4 - ((3 * 5) ^ 2))
    223: (2 || ((5 - 3) || 4)) - 1
    224: 1 * (2 || ((5 - 3) || 4))
    225: 1 - (((3 - 5) || 2) || 4)
    226: 1 + (((4 || 5) / 3) ^ 2)
    227: 1 * (2 || (3 * (4 + 5)))
    228: (2 || ((3 || 4) - 5)) - 1
    229: (5 * (4 || (2 * 3))) - 1
    230: (2 || (3 || (5 - 4))) - 1
    231: (2 || (3 * (5 - 4))) || 1
    232: 1 + (2 || (3 || (5 - 4)))
    233: 1 + ((3 + (4 * 5)) || 2)
    234: (2 || (5 * (3 + 4))) - 1
    235: 1 * (2 || (5 * (3 + 4)))
    236: 1 + (2 || (5 * (3 + 4)))
    237: 1 + (4 * (5 || (3 ^ 2)))
    238: 1 * (2 || ((4 || 3) - 5))
    239: (3 * (5 * (2 ^ 4))) - 1
    240: (2 - (4 - (3 ^ 5))) - 1
    241: (2 || (3 - (4 - 5))) || 1
    242: 1 + (2 - (4 - (3 ^ 5)))
    243: 1 + (2 * ((5 ^ 3) - 4))
    244: 1 + (3 * ((4 + 5) ^ 2))
    245: ((2 * (5 ^ 3)) - 4) - 1
    246: 1 * ((2 * (5 ^ 3)) - 4)
    247: 1 + ((2 * (5 ^ 3)) - 4)
    248: (2 || ((5 || 3) - 4)) - 1
    249: 1 * (2 || ((5 || 3) - 4))
    250: (2 || ((5 || 4) - 3)) - 1
    251: ((5 * (4 - 3)) ^ 2) || 1
    252: 1 + (2 || ((5 || 4) - 3))
    253: ((5 * (2 + 3)) || 4) - 1
    254: (3 * ((2 * 4) || 5)) - 1
    255: 1 * (3 * ((2 * 4) || 5))
    256: (2 || (3 + (5 || 4))) - 1
    257: 1 * (2 || (3 + (5 || 4)))
    258: 1 + (2 || (3 + (5 || 4)))
    259: 1 + (2 * (4 + (5 ^ 3)))
    260: 1 * (2 || (3 * (4 * 5)))
    261: (2 * ((5 - 4) || 3)) || 1
    262: 2 * (((5 - 4) || 3) || 1)
    263: 2 || (3 * (1 + (4 * 5)))
    264: 2 * (1 || (4 * (3 + 5)))
    265: 2 || (5 * (1 + (3 * 4)))
    266: (((5 || 3) || 4) / 2) - 1
    267: 1 / (2 / ((5 || 3) || 4))
    268: 1 + (((5 || 3) || 4) / 2)
    269: (2 * (3 * (4 || 5))) - 1
    270: 1 * (2 * (3 * (4 || 5)))
    271: (2 || ((3 * 4) - 5)) || 1
    272: 1 * ((3 * (4 + 5)) || 2)
    273: 1 + ((3 * (4 + 5)) || 2)
    274: (2 || ((3 + 4) || 5)) - 1
    275: 1 * (2 || ((3 + 4) || 5))
    276: 1 + (2 || ((3 + 4) || 5))
    277: 1 + (2 || ((3 ^ 4) - 5))
    278: 2 * (1 || (3 || (4 + 5)))
    279: (2 * (4 * (3 || 5))) - 1
    280: 1 * (2 * (4 * (3 || 5)))
    281: (2 || (4 * (5 - 3))) || 1
    282: 1 * ((5 || (4 ^ 3)) / 2)
    283: 1 + ((5 || (4 ^ 3)) / 2)
    284: 1 * (2 || ((3 + 5) || 4))
    285: (2 || (5 + (3 ^ 4))) - 1
    286: 1 * (2 || (5 + (3 ^ 4)))
    287: 1 + (2 || (5 + (3 ^ 4)))
    288: (((4 * 5) - 3) ^ 2) - 1
    289: 1 * (((4 * 5) - 3) ^ 2)
    290: 1 + (((4 * 5) - 3) ^ 2)
    291: ((3 || (5 - 4)) - 2) || 1
    292: 1 * (((3 || 4) - 5) || 2)
    293: 1 - ((5 - (3 || 4)) || 2)
    294: 1 + (2 || ((4 + 5) || 3))
    295: 1 - ((3 - (2 ^ 5)) || 4)
    296: 2 * (1 || (3 + (4 || 5)))
    297: ((5 ^ 4) - (3 || 1)) / 2
    298: 2 * (1 || ((5 || 3) - 4))
    299: (3 * (4 * (5 ^ 2))) - 1
    300: ((2 + 5) * (4 || 3)) - 1
    301: (2 * ((4 || 5) / 3)) || 1
    302: 1 + ((2 + 5) * (4 || 3))
    303: 1 * ((5 * (2 + 4)) || 3)
    304: 1 + ((5 * (2 + 4)) || 3)
    305: ((3 || (2 * 5)) - 4) - 1
    306: 1 * ((3 || (2 * 5)) - 4)
    307: 1 + ((3 || (2 * 5)) - 4)
    308: 1 * (2 * ((3 * 5) || 4))
    309: (3 || ((4 * 5) / 2)) - 1
    310: (((5 ^ 4) - 3) / 2) - 1
    311: (2 - (5 - (3 || 4))) || 1
    312: 1 + (((5 ^ 4) - 3) / 2)
    313: 1 + ((3 || (5 - 4)) || 2)
    314: (5 * ((2 + 4) || 3)) - 1
    315: 1 * (5 * ((2 + 4) || 3))
    316: 1 + (5 * ((2 + 4) || 3))
    317: ((3 || (4 * 5)) - 2) - 1
    318: (3 || ((2 || 4) - 5)) - 1
    319: 1 * (3 || ((2 || 4) - 5))
    320: (3 || (2 || (5 - 4))) - 1
    321: ((3 * (5 - 4)) || 2) || 1
    322: 1 + (3 || (2 || (5 - 4)))
    323: (((5 || 4) / 3) ^ 2) - 1
    324: 1 * (((5 || 4) / 3) ^ 2)
    325: 1 + (((5 || 4) / 3) ^ 2)
    326: 1 + (3 || (5 ^ (4 - 2)))
    327: (3 || ((2 ^ 5) - 4)) - 1
    328: 1 * (3 || ((2 ^ 5) - 4))
    329: 1 + (3 || ((2 ^ 5) - 4))
    330: 1 * (3 || (5 * (2 + 4)))
    331: (2 + (3 || (5 - 4))) || 1
    332: 1 * (3 || (4 ^ (5 / 2)))
    333: 1 + (3 || (4 ^ (5 / 2)))
    334: 1 * (3 || ((5 - 2) || 4))
    335: 1 + (3 || ((5 - 2) || 4))
    336: 1 * (3 || (4 + (2 ^ 5)))
    337: 1 + (3 || (4 + (2 ^ 5)))
    338: (((2 + 5) ^ 3) - 4) - 1
    339: 1 * (((2 + 5) ^ 3) - 4)
    340: 1 - (4 - ((2 + 5) ^ 3))
    341: (2 + (4 * (3 + 5))) || 1
    342: ((3 || (4 || 5)) - 2) - 1
    343: 1 * ((3 || (4 || 5)) - 2)
    344: 1 + ((3 || (4 || 5)) - 2)
    345: (3 || ((5 || 1) - 4)) - 2
    346: (2 + (3 || (4 || 5))) - 1
    347: 1 * (2 + (3 || (4 || 5)))
    348: 1 + (2 + (3 || (4 || 5)))
    349: 1 + (3 || ((5 || 2) - 4))
    350: 2 * (1 || ((3 + 4) || 5))
    351: (3 + (4 ^ (5 / 2))) || 1
    352: 1 * ((5 * (3 + 4)) || 2)
    353: 1 + ((5 * (3 + 4)) || 2)
    354: 1 * ((3 + (2 ^ 5)) || 4)
    355: 1 + ((3 + (2 ^ 5)) || 4)
    356: 1 * (2 + (3 || (5 || 4)))
    357: 1 + (2 + (3 || (5 || 4)))
    358: 1 * (3 || (5 || (2 * 4)))
    359: (3 * (5 * (2 || 4))) - 1
    360: ((4 + (3 * 5)) ^ 2) - 1
    361: (((4 + 5) - 3) ^ 2) || 1
    362: 1 + ((4 + (3 * 5)) ^ 2)
    363: (3 || (4 ^ (5 - 2))) - 1
    364: (3 || ((2 + 4) || 5)) - 1
    365: 1 * (3 || ((2 + 4) || 5))
    366: 1 + (3 || ((2 + 4) || 5))
    367: 3 || (((2 + 5) || 1) - 4)
    368: 2 * (1 || ((3 + 5) || 4))
    369: 3 * ((5 ^ (4 - 1)) - 2)
    370: 3 || (2 * ((4 - 1) || 5))
    371: (2 + (5 * (3 + 4))) || 1
    372: (((4 || 2) - 5) || 3) - 1
    373: 1 * (((4 || 2) - 5) || 3)
    374: 1 + (((4 || 2) - 5) || 3)
    375: 1 + (3 || ((2 + 5) || 4))
    376: (1 || (4 * (2 ^ 5))) / 3
    377: 2 + (3 * (5 ^ (4 - 1)))
    378: ((2 || 1) * (5 || 4)) / 3
    379: (3 || (5 * (2 ^ 4))) - 1
    380: (3 || ((4 + 5) ^ 2)) - 1
    381: (2 * (4 + (3 * 5))) || 1
    382: 1 - ((2 - 5) || (3 ^ 4))
    383: 1 - ((5 - (4 || 3)) || 2)
    384: 1 * (3 * (4 * (2 ^ 5)))
    385: 1 + (3 * (4 * (2 ^ 5)))
    386: 1 + (3 || ((2 * 4) || 5))
    387: 2 + (((4 || 1) - 3) || 5)
    388: 3 || (2 * ((4 || 5) - 1))
    389: (3 || (2 * (4 || 5))) - 1
    390: 1 * (3 || (2 * (4 || 5)))
    391: (3 * ((5 || 2) / 4)) || 1
    392: 1 * ((3 || (4 + 5)) || 2)
    393: 1 + ((3 || (4 + 5)) || 2)
    394: (((4 || 2) - 3) || 5) - 1
    395: 1 * (((4 || 2) - 3) || 5)
    396: (((4 * 5) ^ 2) - 3) - 1
    397: 1 * (((4 * 5) ^ 2) - 3)
    398: 1 - (3 - ((4 * 5) ^ 2))
    399: 3 || ((4 * (5 ^ 2)) - 1)
    400: (5 / ((3 / 4) - 1)) ^ 2
    401: (((4 || 5) - 3) - 2) || 1
    402: ((5 * (3 ^ 4)) - 2) - 1
    403: ((5 * (2 ^ 3)) || 4) - 1
    404: 1 * ((5 * (2 ^ 3)) || 4)
    405: (2 * ((4 * 5) || 3)) - 1
    406: 1 * (2 * ((4 * 5) || 3))
    407: 1 + (2 * ((4 * 5) || 3))
    408: 1 + (2 + (5 * (3 ^ 4)))
    409: (4 || (2 + (3 + 5))) - 1
    410: (4 || (5 + (2 * 3))) - 1
    411: (2 + (3 || (4 + 5))) || 1
    412: 1 + (4 || (5 + (2 * 3)))
    413: (4 || (5 + (3 ^ 2))) - 1
    414: 1 * (4 || (5 + (3 ^ 2)))
    415: (4 || (2 * (3 + 5))) - 1
    416: 1 * (4 || (2 * (3 + 5)))
    417: 1 + (4 || (2 * (3 + 5)))
    418: 1 + (2 + (4 || (3 * 5)))
    419: 1 - (5 - ((4 || 2) || 3))
    420: (4 || (3 * (2 + 5))) - 1
    421: ((3 - (4 - 5)) || 2) || 1
    422: 1 + (4 || (3 * (2 + 5)))
    423: (2 * (4 * (5 || 3))) - 1
    424: 1 * (2 * (4 * (5 || 3)))
    425: 1 + (2 * (4 * (5 || 3)))
    426: 1 + (4 || (5 * (2 + 3)))
    427: (3 + (4 || (5 ^ 2))) - 1
    428: ((4 || (2 ^ 5)) - 3) - 1
    429: 1 * ((4 || (2 ^ 5)) - 3)
    430: 1 - (3 - (4 || (2 ^ 5)))
    431: ((5 + (3 ^ 4)) / 2) || 1
    432: ((4 || (3 || 5)) - 2) - 1
    433: 1 * ((4 || (3 || 5)) - 2)
    434: 1 + ((4 || (3 || 5)) - 2)
    435: 1 * (3 + (4 || (2 ^ 5)))
    436: 1 + (3 + (4 || (2 ^ 5)))
    437: 1 * (2 + (4 || (3 || 5)))
    438: 1 + (2 + (4 || (3 || 5)))
    439: (4 || (5 * (2 ^ 3))) - 1
    440: 1 * (4 || (5 * (2 ^ 3)))
    441: (2 + ((4 || 5) - 3)) || 1
    442: (3 + (4 || (1 ^ 5))) || 2
    443: (4 || (3 * (1 || 5))) - 2
    444: (4 || (5 * (3 ^ 2))) - 1
    445: 1 * (4 || (5 * (3 ^ 2)))
    446: 1 + (4 || (5 * (3 ^ 2)))
    447: ((2 + 5) * (4 ^ 3)) - 1
    448: (((4 || 5) || 2) - 3) - 1
    449: 1 * (((4 || 5) || 2) - 3)
    450: (((4 || 5) || 3) - 2) - 1
    451: (((5 || 2) - 4) - 3) || 1
    452: 1 + (((4 || 5) || 3) - 2)
    453: ((5 * (3 ^ 2)) || 4) - 1
    454: 1 * ((5 * (3 ^ 2)) || 4)
    455: 1 + ((5 * (3 ^ 2)) || 4)
    456: 1 + (2 + ((4 || 5) || 3))
    457: 1 + (4 || (5 || (2 * 3)))
    458: 1 * (4 || (5 || (2 ^ 3)))
    459: (4 * (5 * (2 || 3))) - 1
    460: 1 * (4 * (5 * (2 || 3)))
    461: (2 * (3 + (4 * 5))) || 1
    462: 2 * ((3 + (4 * 5)) || 1)
    463: (4 || ((3 + 5) ^ 2)) - 1
    464: (4 || ((2 * 3) || 5)) - 1
    465: 1 * (4 || ((2 * 3) || 5))
    466: 1 + (4 || ((2 * 3) || 5))
    467: 2 + (4 || (5 * (1 || 3)))
    468: ((2 + (4 || 5)) || 1) - 3
    469: (4 || (2 * (3 || 5))) - 1
    470: 1 * (4 || (2 * (3 || 5)))
    471: (((5 || 3) - 4) - 2) || 1
    472: ((2 + (4 || 5)) || 3) - 1
    473: 1 * ((2 + (4 || 5)) || 3)
    474: 1 + ((2 + (4 || 5)) || 3)
    475: 1 * (4 || (3 * (5 ^ 2)))
    476: 1 + (4 || (3 * (5 ^ 2)))
    477: (2 * ((3 ^ 5) - 4)) - 1
    478: 1 * (2 * ((3 ^ 5) - 4))
    479: 1 - (2 * (4 - (3 ^ 5)))
    480: 2 * (1 - (4 - (3 ^ 5)))
    481: (2 * ((5 - 3) || 4)) || 1
    482: 1 * ((3 + (4 || 5)) || 2)
    483: 1 - (4 - (2 * (3 ^ 5)))
    484: (4 || ((2 ^ 3) || 5)) - 1
    485: 1 * (4 || ((2 ^ 3) || 5))
    486: 1 + (4 || ((2 ^ 3) || 5))
    487: 1 + ((4 * (3 ^ 5)) / 2)
    488: 2 * ((1 ^ 4) + (3 ^ 5))
    489: (4 + (2 * (3 ^ 5))) - 1
    490: 1 * (4 + (2 * (3 ^ 5)))
    491: (((5 || 4) - 3) - 2) || 1
    492: 1 * (((5 || 3) - 4) || 2)
    493: 1 - ((4 - (5 || 3)) || 2)
    494: 1 * (2 * (4 + (3 ^ 5)))
    495: 1 + (2 * (4 + (3 ^ 5)))
    496: 1 + (3 * ((2 ^ 4) || 5))
    497: ((4 * (5 ^ 3)) - 2) - 1
    498: 1 * ((4 * (5 ^ 3)) - 2)
    499: 1 - (2 - (4 * (5 ^ 3)))
    500: ((1 + (4 + 5)) ^ 3) / 2
    501: (2 + (3 + (4 || 5))) || 1
    502: 1 * (2 + (4 * (5 ^ 3)))
    503: 1 + (2 + (4 * (5 ^ 3)))
    504: 2 * (4 * ((1 + 5) || 3))
    505: (((5 || 1) || 2) - 4) - 3
    506: (((2 * 4) ^ 3) - 5) - 1
    507: (4 * (2 + (5 ^ 3))) - 1
    508: ((2 ^ (4 + 5)) - 3) - 1
    509: ((5 || (3 * 4)) - 2) - 1
    510: (5 || (3 + (2 * 4))) - 1
    511: (2 - (4 - (5 || 3))) || 1
    512: 1 + (5 || (3 + (2 * 4)))
    513: 1 * ((5 || (2 ^ 4)) - 3)
    514: 1 + ((5 || (2 ^ 4)) - 3)
    515: 1 * (3 + (2 ^ (4 + 5)))
    516: (5 || ((3 || 4) / 2)) - 1
    517: 1 * (5 || ((3 || 4) / 2))
    518: 1 + (5 || ((3 || 4) / 2))
    519: 1 + (5 || (3 * (2 + 4)))
    520: (((5 || 2) || 4) - 3) - 1
    521: ((5 * (4 - 3)) || 2) || 1
    522: 1 + (((5 || 2) || 4) - 3)
    523: (5 || (2 * (3 * 4))) - 1
    524: 1 * (5 || (2 * (3 * 4)))
    525: 1 + (5 || (2 * (3 * 4)))
    526: (3 + ((5 || 2) || 4)) - 1
    527: 1 * (3 + ((5 || 2) || 4))
    528: ((3 + (4 * 5)) ^ 2) - 1
    529: 1 * ((3 + (4 * 5)) ^ 2)
    530: 1 + ((3 + (4 * 5)) ^ 2)
    531: (2 + ((5 || 4) - 3)) || 1
    532: 1 * (((5 || 3) || 4) - 2)
    533: 1 + (((5 || 3) || 4) - 2)
    534: (2 + (5 || (1 ^ 3))) || 4
    535: (2 + ((5 || 3) || 4)) - 1
    536: 1 * (2 + ((5 || 3) || 4))
    537: 1 + (2 + ((5 || 3) || 4))
    538: (((5 || 4) || 2) - 3) - 1
    539: 1 * (((5 || 4) || 2) - 3)
    540: (((5 || 4) || 3) - 2) - 1
    541: (2 * (3 * (4 + 5))) || 1
    542: 1 + (((5 || 4) || 3) - 2)
    543: 2 + (5 || (4 || (1 ^ 3)))
    544: (2 + ((5 || 4) || 3)) - 1
    545: 1 * (2 + ((5 || 4) || 3))
    546: 1 + (2 + ((5 || 4) || 3))
    547: 1 + (5 || (4 || (2 * 3)))
    548: (5 || ((3 + 4) ^ 2)) - 1
    549: 1 * (5 || ((3 + 4) ^ 2))
    550: 1 + (5 || ((3 + 4) ^ 2))
    551: ((3 + (5 || 4)) - 2) || 1
    552: (4 + (5 || (1 ^ 3))) || 2
    553: ((2 + (5 || 3)) || 4) - 1
    554: 1 * ((2 + (5 || 3)) || 4)
    555: 1 + ((2 + (5 || 3)) || 4)
    556: 5 || ((1 || (3 * 4)) / 2)
    557: ((5 || (2 * 3)) || 1) - 4
    558: (5 * (1 || (3 * 4))) - 2
    559: ((2 ^ 4) * (3 || 5)) - 1
    560: 1 * ((2 ^ 4) * (3 || 5))
    561: (4 * (5 + (3 ^ 2))) || 1
    562: ((2 + (5 || 4)) || 3) - 1
    563: 1 * ((2 + (5 || 4)) || 3)
    564: 1 + ((2 + (5 || 4)) || 3)
    565: 1 + ((5 || (2 * 3)) || 4)
    566: 1 * (2 + (5 || (4 ^ 3)))
    567: 1 + (2 + (5 || (4 ^ 3)))
    568: 1 * (5 || (2 * (3 || 4)))
    569: 1 + (5 || (2 * (3 || 4)))
    570: (1 || (4 * (3 || 5))) / 2
    571: (((4 ^ 3) - 5) - 2) || 1
    572: 1 * ((3 + (5 || 4)) || 2)
    573: 1 + ((3 + (5 || 4)) || 2)
    574: (1 + (5 || (2 * 3))) || 4
    575: (((5 - 3) || 4) ^ 2) - 1
    576: 1 * (((5 - 3) || 4) ^ 2)
    577: 1 + (((5 - 3) || 4) ^ 2)
    578: ((5 || (3 ^ 4)) - 2) - 1
    579: 1 * ((5 || (3 ^ 4)) - 2)
    580: 1 - (2 - (5 || (3 ^ 4)))
    581: (2 * ((3 || 4) - 5)) || 1
    582: (2 + (5 || (3 ^ 4))) - 1
    583: 1 * (2 + (5 || (3 ^ 4)))
    584: 1 + (2 + (5 || (3 ^ 4)))
    585: 1 + ((5 || (2 ^ 3)) || 4)
    586: 1 * (5 || (2 * (4 || 3)))
    587: 1 + (5 || (2 * (4 || 3)))
    588: 3 * (((1 ^ 5) || 4) ^ 2)
    589: (((4 ^ 3) - 5) || 1) - 2
    590: 5 * (1 || (3 * (2 + 4)))
    591: (2 + (3 + (5 || 4))) || 1
    592: 1 * (((4 ^ 3) - 5) || 2)
    593: 1 + (((4 ^ 3) - 5) || 2)
    594: 1 * ((5 || (3 ^ 2)) || 4)
    595: 1 + ((5 || (3 ^ 2)) || 4)
    596: 2 + ((5 ^ 4) - (3 || 1))
    597: 3 * (((4 * 5) || 1) - 2)
    598: (5 ^ 4) - (3 ^ (1 + 2))
    599: ((3 * (4 * 5)) || 1) - 2
    600: 5 * (1 || (4 * (2 + 3)))
    601: (4 * ((3 - 2) || 5)) || 1
    602: 1 * ((3 * (4 * 5)) || 2)
    603: 1 + ((3 * (4 * 5)) || 2)
    604: 4 * (((3 - 2) || 5) || 1)
    605: (3 * ((4 * 5) || 2)) - 1
    606: 1 * (3 * ((4 * 5) || 2))
    607: 1 + (3 * ((4 * 5) || 2))
    608: 1 * (4 * ((3 * 5) || 2))
    609: 1 + (4 * ((3 * 5) || 2))
    610: 1 * (5 * ((3 * 4) || 2))
    611: (2 + ((4 ^ 3) - 5)) || 1
    612: (((4 + 5) - 3) || 1) || 2
    613: (3 * (5 * (4 || 1))) - 2
    614: ((2 + 4) || (3 * 5)) - 1
    615: 1 * ((2 + 4) || (3 * 5))
    616: 1 + ((2 + 4) || (3 * 5))
    617: 1 + ((5 ^ 4) - (3 ^ 2))
    618: ((5 ^ 4) - (2 * 3)) - 1
    619: (((5 ^ 4) - 3) - 2) - 1
    620: 1 * (((5 ^ 4) - 3) - 2)
    621: (2 * (3 || (5 - 4))) || 1
    622: 2 * ((3 || (5 - 4)) || 1)
    623: (2 - (3 - (5 ^ 4))) - 1
    624: 1 * (2 - (3 - (5 ^ 4)))
    625: ((3 + (5 ^ 4)) - 2) - 1
    626: 1 * ((3 + (5 ^ 4)) - 2)
    627: 1 + ((3 + (5 ^ 4)) - 2)
    628: 1 + (((5 ^ 3) || 4) / 2)
    629: (2 + (3 + (5 ^ 4))) - 1
    630: ((2 * 3) + (5 ^ 4)) - 1
    631: (3 * (2 || (5 - 4))) || 1
    632: 1 + ((2 * 3) + (5 ^ 4))
    633: ((3 ^ 2) + (5 ^ 4)) - 1
    634: 1 * ((3 ^ 2) + (5 ^ 4))
    635: 1 + ((3 ^ 2) + (5 ^ 4))
    636: 1 + (((2 + 4) || 3) || 5)
    637: 1 * (((4 ^ 3) || 2) - 5)
    638: 1 - (5 - ((4 ^ 3) || 2))
    639: (2 * (3 || (4 * 5))) - 1
    640: 1 * (2 * (3 || (4 * 5)))
    641: (2 ^ ((4 + 5) - 3)) || 1
    642: (((4 ^ 3) || 5) - 2) - 1
    643: 1 * (((4 ^ 3) || 5) - 2)
    644: 1 + (((4 ^ 3) || 5) - 2)
    645: 1 + (((3 + 5) ^ 2) || 4)
    646: 1 + (((2 * 3) || 4) || 5)
    647: ((2 || 3) + (5 ^ 4)) - 1
    648: 1 * ((2 || 3) + (5 ^ 4))
    649: 1 + ((2 || 3) + (5 ^ 4))
    650: 2 * (3 || (5 * (1 + 4)))
    651: (5 * ((2 ^ 4) - 3)) || 1
    652: (((2 + 4) || 5) || 3) - 1
    653: 1 * (((2 + 4) || 5) || 3)
    654: 1 + (((2 + 4) || 5) || 3)
    655: 1 + (((2 * 3) || 5) || 4)
    656: ((3 || 2) + (5 ^ 4)) - 1
    657: 1 * ((3 || 2) + (5 ^ 4))
    658: 1 + ((3 || 2) + (5 ^ 4))
    659: (3 * (2 || (4 * 5))) - 1
    660: 1 * (3 * (2 || (4 * 5)))
    661: (3 * (2 + (4 * 5))) || 1
    662: (((3 + 4) || 1) - 5) || 2
    663: 3 * ((2 + (4 * 5)) || 1)
    664: ((2 + (4 ^ 3)) || 5) - 1
    665: 1 * ((2 + (4 ^ 3)) || 5)
    666: 1 + ((2 + (4 ^ 3)) || 5)
    667: (4 || 2) + (5 ^ (1 + 3))
    668: (5 * (1 || (3 || 4))) - 2

Bonus 3: If we extend this to include 6 ([output](https://pastebin.com/raw/BiCA2cCe)), we cover 9965 of the first 10000, the first one we fail to make isn't until 5989.