From my experience with tailscale so far - there are so many different ways to have it configured well. If it works well for you having it on the host, then go for it. I have home assistant in a VM with tailscale and tailscale on the (windows) host. This works well for my needs and I don’t mind having it running “twice”

Multiple versions, paths, and installs of Python. Using pip makes it worse.

I still don’t fully understand how to gracefully have multiple desktop environments and switch between them. When I want to try something new to me like lxqt, I usually spin up a VM.

Two actually

Can you tell me more about that TV?

If you do compile something, it is very easy to make it an installable package you could share. I’m not sure how the repos are managed

I chose to set up grafana, mqtt, etc for an RV instead of home assistant. Little more lightweight for the raspberry pi 3 I used. Pulling together solar info, so we could see how long the AC would keep running on the road