Use the buddy system. Years ago I had a work-friend, we'd just book meetings with each other a couple of times a week, go to a meeting room and just hang out, I taught him to juggle, or we'd watch an episode from a series etc.

It was fun feeling like we got away with something, but realistically nobody questioned it because we both got our work done and it was a good company where that mattered more than time spent at a desk.

Another option you could consider is rather than running the VPN on the pi and downloading through that, to run the VPN on your media server as you planned and instead use the pi (or your router if you can run openwrt) as the remote access point. Then you only need to worry about the performance needed for remote access

I'm not sure how tailscale works, but this is what I do with zerotier (i.e. run it on my router).

I mainly use my pc to play games, maybe 90% works fine but that 10% is still quite a lot. Also, even if the games themselves work sometimes extra tools (like overlays) around them don't, which is the case for my main game.

Lastly I have struggled with X11 in the past so much with my multiple different resolution and refresh rate monitors working, and it doesn't seem like Wayland is there yet either.

I look forward to these things being ironed out, it has come a very long way in the past few years, I do believe a couple more and I'll be able to switch back to Linux.

I understand that, but just because I'm capable of working with a less friendly system doesn't mean it's a good thing. If anything I'd still list it as a negative aspect that it requires more knowledge and research.

If there was a question with an answer like "I'm looking for a challenge" it'd make sense that it's listed as a positive.

"Requires reading up in manuals for usage" why is this considered a pro..?