I have a laptop and a desktop-based-server on a 192.168.1.x segment on my network. I want to setup Tailscale between them.
Will it be bad if Tailscale connects while my laptop is local, on 192.168.1.x network?
Can I make it automatically connect via Tailscale when away and via the local network when home?
How can I best test the Tailscale network while I am at home?
It will be fine. If two computers are on the same lan, they will connect directly using your local network. If they are on two different networks, they will reroute through their network.