2. I set up Webfinger first, so assuming you're setting it up from scratch you can either run a Webfinger server yourself, or just configure the paths in whatever web server you have for your base domain. I didn't feel like running Yet Another Server and since the Tailnet's only for me I just plugged the following section into Caddy:
Where webfinger.json is file containing the response tailscale is looking for from their doc. You can verify it works right at https://webfinger.net/lookup/ .