That judgment is partly outside the more mechanical parts of cryptography. You have to see what your application domain demands.
OTR is just the first example I could think of, that gives different guarantees than most normal cryptosystems. I don't particularly recommend it for anything apart from instant messaging. And I wouldn't recommend implementing your own.
If I speak to you in private (and we know each other), you can be sure you are speaking to me, but you won't be able to proof to any third party anything I said. OTR can give you something like that. PGP can't.
For most application you will be well served with PGP or TLS. But be aware of what baggage they bring. For some areas losing deniability via PGP can be worse than plain text.
This is a counterfeit argument. PGP loses "deniability" (and "forward secrecy") if by PGP you mean "the PGP user interface". But if what you mean is simply "the PGP cryptosystem" and "the PGP message format of packets and bulk encryption and signatures", then you can grant your system most any property OTR gives you.
This is a moot point, because most systems would never care enough to intricately position all their features just-so to compose OTR-like features out of PGP primitives. What they need is to be able to encrypt anything without implementing trivially exploitable crypto vulnerabilities that were discovered and solved decades ago.
This is a textbook case of everyone's good being strangled by someone's opinion of the perfect.
I don't disagree with you. And OTR is just one example, and may even be a straw-man by now. Just be aware that there are other valid choices for cryptosystems, while you still don't have to roll your own.
OTR is just the first example I could think of, that gives different guarantees than most normal cryptosystems. I don't particularly recommend it for anything apart from instant messaging. And I wouldn't recommend implementing your own.
If I speak to you in private (and we know each other), you can be sure you are speaking to me, but you won't be able to proof to any third party anything I said. OTR can give you something like that. PGP can't.
For most application you will be well served with PGP or TLS. But be aware of what baggage they bring. For some areas losing deniability via PGP can be worse than plain text.