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https://tailscale.com/kb/1054/dns#nameservers
and
https://tailscale.com/kb/1114/pi-hole#step-3-set-your-raspberry-pi-as-your-dns-server
Set tailscale to use your dns server to resolve your services (or all traffic if you prefer). Assuming your dns server is on 100.x.x.1:53, then put 100.x.x.1 as a nameserver.
I set that up, but the issue now is that my DNS server is replying back with the private IP, which is not accessible from tailscale.
EDIT: Figured this one out. Need to advertise the routes from one of my machines. Set that up and I am good to go now. Thanks!