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Afaik tailscale will work with CGNAT and you can get your own router to sort out DHCP (or just pihole on your server?). Others can probably provide better answer
Wouldn't that cause a problem with two DHCPs being active?
Honestly I think someone else should answer this, but I believe you can just use different IP range (example 192.168.0.x on ISP device and 192.168.1.x on new router). Reading other comment it looks like its not the best idea, but we have that kind of setup in office and it works fine. There is no selfhosting involved tho
You don't use VLANs to separate traffic?
You connect them in a chain.