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I have played with GPG time and again, my Enigmail/Thunderbird/OpenPGP card setup is fully functional.

But what's holding me back is webmail.

I don't use the web interface often, but it has proven to be absolutely crucial to be able to get some important mail (boarding pass, mail explaining how to get somewhere etc.) from any computer.

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you need a cross-platform USB stick program, with all your secrets on it encrypted properly, for that kind of thing. (The simplest hack I can think of would probably be python binaries, with a local-webserver based interface.)

I don't know of such an application, or whether the approach is rigorous, I'm afraid. But I think that's the shape of the solution.

Doesn't help.

First, I'm not remotely interested in running my own mail infrastructur anymore. Been there, done that. Today it's much too hard to get mails accepted by others.

But more important: iPads don't have an USB connector, my mobile phone doesn't have one. Friends have Macs, in other places there might be other crippled devices.

The web is a universal building block. USB sticks are not.

I use Lastpass, which has a client for most platforms.

They could be compromised, but they claim all data is encrypted locally before being sent to their servers. I have not verified that claim.

A password manager does not encrypt or sign mails.

Sorry, I wasn't clear. I use last pass to transfer my private key to the PGP app on my iPad (and elsewhere) (as opposed going through Dropbox or whatever).

Relies upon trusting last pass and trusting the iPad of course, both of which are questionable.

My friend's computers don't have PGP installed. Neither do "surf terminals". I certainly cannot install PGP there.

Everything that requires some special software to run is a non-starter.

Why rely on the (possibly compromised) OS of the host computer's hard drive when you can boot your own OS straight from the USB itself? What you are looking for is tails (https://tails.boum.org/) with a luks encrypted persistent partition.