I followed a similar trajectory for similar reasons. I was playing with wireguard around 2020 when I learned of Tailscale and since then haven't looked back.
Just the other day I was able to set my sister up with access to my Plex server and the ability to piggyback on my UK internet connection to stream BBC/Channel 4 content from Australia. It took all of 5 minutes to get it working.
Same trajectory, but I've now migrated a lot of my previous tailscale stuff to Cloudflare tunnels -- it opens up the attack vector a _little_ bit (that can be mitigated) and it's app-free (which made it viable for a lot of my non-tech users). Still love tailscale and use it all the time for remote access to very sensitive stuff (ssh).
Interesting. I've obviously heard Cloudflare tunnel, but haven't looked into beyond knowing that it exists. Was going "app-free" the primary motivator in your case for the switch?
I have a few services I've configured static routes for on my router (so my wife can access them without needing to have her phone connected to Tailscale all the time), but other than that it's never been much of a pain point.
Yeah, the app-free nature of tunnels was a huge draw. Cloudflare does effectively MiTM your traffic, so that's a risk you have accept but the tradeoff was worth it for me. Between that an the secondary authentication you can put in front of your services, I felt much better about opening my self-hosted stuff to to relative 'public'.
Just the other day I was able to set my sister up with access to my Plex server and the ability to piggyback on my UK internet connection to stream BBC/Channel 4 content from Australia. It took all of 5 minutes to get it working.