Just curious, what about scp-ing to your server is less than ideal for you? I would think a static server with nginx or similar would be an easy one time setup and then you do a single command to scp to it whenever you want to add images. No redeploy necessary. I would almost consider that easier than other bespoke solutions that you would have to learn

I can’t compare to fastmail since I haven’t used it, but I’ve been very happy with proton mail.

Have you looked into pressure advance calibration?

I’m definitely in the “for almost everything” camp. It’s less ambiguous especially when you consider the DD/MM vs MM/DD nonsense between US dates vs elsewhere. Pretty much the only time I don’t use ISO-8601 is when I’m using non-numeric month names like when saying a date out loud.