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Partial (We're almost there! Oh boy will daddy be proud!)

Beast = GRYPHON, shouts = ROAR, sympathise = PITY, medicine = HERB, old friend = AI (from earlier, see robocop.txt). These fit a crossword near the top left corner.

LITERATE HEROES

The crossword with solutions:

enter image description here

Partial (We're almost there! Oh boy will daddy be proud!)

Beast = GRYPHON, shouts = ROAR, sympathise = PITY, medicine = HERB, old friend = AI (from earlier, see robocop.txt)

LITERATE HEROES

Beast = GRYPHON, shouts = ROAR, sympathise = PITY, medicine = HERB, old friend = AI (from earlier, see robocop.txt). These fit a crossword near the top left corner.

LITERATE HEROES

The crossword with solutions:

enter image description here

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Jafe
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?. This is a fancy way of cursing (4) -> dang
?. This one expresses happiness (2) -> XD (from Ben J)
?. Oh, that's a long number. And if you read it backwards, it would be even longer. (2) -> ip
?. This is something wet, but in the Internet, it meant something else... (4) -> dank (from Ben J)

enter image description here

We're left with

The letters HEROES.

...anagram to LITERATE. Not sure how this helps yet...

So the 15-character password could be

LITERATE HEROES

?. This is a fancy way of cursing (4) -> dang
?. This one expresses happiness (2) -> XD (from Ben J)
?. Oh, that's a long number. And if you read it backwards, it would be even longer. (2) -> ip
?. This is something wet, but in the Internet, it meant something else... (4) -> dank (from Ben J)

...anagram to LITERATE. Not sure how this helps yet...

?. This is a fancy way of cursing (4) -> dang
?. This one expresses happiness (2) -> XD (from Ben J)
?. Oh, that's a long number. And if you read it backwards, it would be even longer. (2) -> ip
?. This is something wet, but in the Internet, it meant something else... (4) -> dank (from Ben J)

enter image description here

We're left with

The letters HEROES.

...anagram to LITERATE.

So the 15-character password could be

LITERATE HEROES

added 10 characters in body
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Jafe
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?. This is a fancy way of cursing (4) -> darn/goshdang?
?. This one expresses happiness (2) -> XD (from Ben J)
?. Oh, that's a long number. And if you read it backwards, it would be even longer. (2) -> ip
?. This is something wet, but in the Internet, it meant something else... (4) -> ?dank (from Ben J)

?. This is a fancy way of cursing (4) -> darn/gosh?
?. This one expresses happiness (2) -> XD (from Ben J)
?. Oh, that's a long number. And if you read it backwards, it would be even longer. (2) -> ip
?. This is something wet, but in the Internet, it meant something else... (4) -> ?

?. This is a fancy way of cursing (4) -> dang
?. This one expresses happiness (2) -> XD (from Ben J)
?. Oh, that's a long number. And if you read it backwards, it would be even longer. (2) -> ip
?. This is something wet, but in the Internet, it meant something else... (4) -> dank (from Ben J)

Bounty Ended with 100 reputation awarded by Thomas Blue
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