I'm just running a dnsmasq and using that to alias machines / workloads. For my network I needed to make sure a route to the dnsmasq IP is advertised by a subnet router and then I told tailscale to "override local dns" and make all tailscale clients use that dnsmasq IP as their DNS server.

I have a mix of bare machines and load-balanced workloads behind an nginx-ingress, all with names specified in the dnsmasq config, and because everything on the tailnet resolves names through dnsmasq (and routes through tailscale), everything works beautifully.

I'm still looking forward to this caddy integration, though.