Disc brakes add some $$, but are worth it if you have long descents or regularly wet weather. Don’t be afraid of rim brakes, though, if you are a fair weather biker.

Also consider looking at touring bikes. You’ll get wider tires, good gearing, and more robust frames. Might get a good second hand value, or some luck with sales if those styles aren’t popular at your LBS.

If you are in the US, check any Aldis near you. No joke, got a quality stand for like $40, and it collapses down to fit in a corner or closet.

I have a J&G rain cape. It is really great - thumb loops means you have a little dry cabin (protip: if you have a spot on your handlebars to hook the loops, it keeps your arms dryer). Yes, if you are going fast it does have a little resistance. BUT, it also breaths much much better than any rain jacket I’ve ever had. So you don’t get nearly as clammy or sweaty. To me, that’s a worthwhile tradeoff.

How many users do you serve with that Plex box?

Keep tabs on https://rpilocator.com/ to check stock of Pi retailers around the globe.