Holy wall of .txt! This is extremely partial but might as well get this going. I'm going to go out on a limb and guess that the starting point is
...starthere.txt (shocking, I know)
So, let's try to solve the clues:
0) A surficial excuse for discrimination (4) -> race?
1) When I .... about politics you always seem to .... (4/4)
2) Italy relative to Switzerland (2) -> se (southeast)?
2) Way to get loved for quite some time, time, time (4) -> stay (according to Taylor Swift)
3) A letter, best fitting Poseidon (3) -> psi, which looks like a trident
3) Vatican relative to Italy (2) -> in?
The crossword seems to be the one in the centre of the image (the 4x4 with numbers 0-3).
Continuing where pirate and Omega Krypton left off...
For gryphon:
Take the outside letters plus T, SKYPAWNT (up = SKY, legs = PAWS, sunny = TAN?)
For oceanman:
Take the inside letters plus T, STAALSIT (holy = ST, seawater = SALT, travel = SAIL?)