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.

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

Can I request a hack? How do I handle several different versions of Python installed, which one is used for pip stuff, and how sudo/running as services changes all of this.

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

I mainly use them when I want something windowed but without tabs taking up space. Like monitoring my solar panels

Any idea how to get links clicked in a PWA like Google Messages to open in a normal browser tab? I’ve tried nothing.

If you are concerned about things like PWAs like I was, try it out anyway. PWAs require a bit more setup, but are a lot more flexible in Firefox. For example, PWAs with http connections have a huge banner in Chrome, and just an icon in Firefox. Everything I’ve noticed is that firefox is just as snappy as Chrome

I think I had a similar problem a couple weeks ago. Make sure they are adding the device to your tailnet, by default it adds the new machine to their own tailnet. I know I hit some kind of issue like that, at least.