You make a very good argument for Tailscale, and I think I’ll definitely be looking deeper into that.
I like your suggestion to map out functional requirements, and then go from there. I think I’ll go ahead and start working on a decent map for that.
As far as the new router for pi-hole… my super-great, wonderful, most awesome ISP (I hope the sarcasm is evident, haha; the provider is AT&T) dictates that I use their specific modem/router (not optional), and they also do not allow me to change DHCP on that mandated hardware. So my best option, so far as I’ve seen, is to use the ISP’s box in pass-through with a better router behind it that I can actually set up to use pi-hole.
Thank you for your thoughts and suggestions! I’m going to take a deeper look at Tailscale and get started properly mapping high-level needs/wants out, with options for each.