Earlier quoted context omitted.
This is not a realistic solution. SMS-sized messages are the least hard part of this for me. What I want is to be able to point at a file or folder on my computer and say, "sign that with a public key so I can prove I wrote it" or "encrypt that with someone else's public key so only they can read it". At that point, I don't necessary care all that much about how the file gets sent over the network. It doesn't need to…
You asked (among other things) how to send messages securely without PGP. Don't use PGP to send secure messages; use a secure messenger, like Signal or Wire. Someone else asked how to email securely without PGP. Email isn't secure with PGP. Don't use PGP to send encrypt emails, and don't use email to send secure messages; use a secure messenger, like Signal or Wire. I acknowledge there are use cases not well covered…
Do you know of any projects that are aiming to solve this? It feels like all that is needed is a halfway decent standard file format, and some tools to bootstrap it. That seems to be how we got TLS and SSH, which are the two successes of encryption.
I suppose those two protocols have the advantage of interactive negotiation. Whereas software encrypting a file does not get to negotiate any parameters with the software that will later be decrypting it.
Moreover, those protocols had some decent weight behind it. Secure data transport is a problem that matters to essentially everyone these days. Whereas secure and portable file encryption really does not. E-mail is a significant use-case, but only tangentially, and optimal E-mail solutions are not really optimal portable file solutions.