Rather than being frustrated you should consider that you're holding on to something that is an inelegant relic of another age. There are things PGP/GPG do that need replacements, but those replacements need to be very different to PGP.
1. I've fethed around with PGP since Zimmerman published the source code, and I attest that setting it up properly is not simple. Not as difficult as creating an x509 certificate in OpenSSL with SANs, but really not straight forward. But the real difficulty is actually using it.
1.1 Trusting in-browser crypto like mailvelope is bizarre. mailpile was a better approach, but they seem to have lost momentum.
2.1 The only significant use for PGP is signing linux packages and git code signing. But this is terrible as a breach means you could generate whole trees of fake checkins, and it desperately needs something like Signal's ratchet mechanism, or (heaven forbid) a blockchain.
2.2 If you want to send something on a USB stick then encrypting it with a sensible and usable tool (with modern AEAD encryption) like https://github.com/FiloSottile/age will be far more reliable.
3 You have no basis for this speculation. Signal are clear that they don't hold your data, and I really can't see 'compelled speech' like writing a backdoor being possible. Signal is as capable of resisting analysis as anything else that's around, far better than PGP, to the point that your security is essentially as good as you and your correspondents device security.
1. I've fethed around with PGP since Zimmerman published the source code, and I attest that setting it up properly is not simple. Not as difficult as creating an x509 certificate in OpenSSL with SANs, but really not straight forward. But the real difficulty is actually using it. 1.1 Trusting in-browser crypto like mailvelope is bizarre. mailpile was a better approach, but they seem to have lost momentum.
2.1 The only significant use for PGP is signing linux packages and git code signing. But this is terrible as a breach means you could generate whole trees of fake checkins, and it desperately needs something like Signal's ratchet mechanism, or (heaven forbid) a blockchain. 2.2 If you want to send something on a USB stick then encrypting it with a sensible and usable tool (with modern AEAD encryption) like https://github.com/FiloSottile/age will be far more reliable.
3 You have no basis for this speculation. Signal are clear that they don't hold your data, and I really can't see 'compelled speech' like writing a backdoor being possible. Signal is as capable of resisting analysis as anything else that's around, far better than PGP, to the point that your security is essentially as good as you and your correspondents device security.