Is pass able to decrypt ssh key files, or trick the user into decrypting them?
One of the files in the example is not a pass encrypted file but an ssh private key ("id_ed25519"). ssh private keys are either unencrypted or encrypted with a passphrase (but not via GPG in any case, and GPG of course is what pass uses).
The only way the outlined attack would be better than just uploading via curl is if pass could somehow enable the attacker to get a decrypted ssh private key. But I can't imagine why pass would be capable of doing that.