NAT breaking, I can have a wireguard network with Tailscale where every device only has an RFC1918 address and a default route.

not having to generate, manage, and distribute wireguard secrets and configurations was good enough reason for me to switch.

Tailscale also provides a "magic DNS" service which lets you resolve your Tailscale device names without setting up unbound etc, and which can relay other requests through to your pi-hole or unbound or whatever, which can then listen only on the tailscale IP address, so no need to run an open resolver or deal with source IP filtering.

e: also, you can share devices between tailscale users without generating, managing, distributing wireguard secrets. You send your pal/partner/kid a link and they can access your fileserver or raspberry pi webserver or pihole server for themselves wherever they are.

> For a Linux user, you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, and then using SVN or CVS on the mounted filesystem. From Windows or Mac, this FTP account could be accessed through built-in software.

I do the same, for multiple domains I own. Definitely not difficult.