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.