Tailscale is a sort of VPN. So, yeah, treat it the same.
I’m mostly responding to add a little context to the security concerns. Probably the biggest inside-the-VPN concern is that someone on your VPN gets some malware. So, if this is your family network, and say, your kid’s phone or laptop gets some malware, now any non-encrypted traffic is potentially compromised. Basically, the VPN is only as secure as the weakest link. That’s the thing you’re protecting against with https for individual services.
If I were hosting vaultwarden, and had my bank login in there, I absolutely wouldn’t consider a VPN + http sufficient protection. With LLMs, if we don’t have malware that knows how to hunt around for valuable credentials in the wild already, it’ll be here soon. I personally run my Jellyfin server over https because I’ve gone to the trouble to set up a good system to use letsencrypt with nginx as a proxy for any service. But I wouldn’t be too worried about running Jellyfin over http.





You can use git over ssh with no other infrastructure. It’s less work, and you’ll learn more from doing it.