alt Hacker Newsi’m assuming because of the “web server hosting photos”. Probably Immich if i had to guess?
tailscale is fine if you’re somewhat tech savvy, but it’s annoying to show all your friends and family how to “correctly” access your web server. Too much friction. First download the tailscale app, sign in, blah blah. Then you also are unnecessarily bogging down everyone’s smartphone with a wire guard VPN profile which is…undesirable.
I like tailscale and use it for some stuff. But for web servers that i want my whole family (and some friends) to easily access, a traditional setup makes much more sense. The tradeoff is (obviously) a higher security burden. I protect the web apps in my homelab with SSO (OIDC), among other things.
I prefer to gatekeep "entry points" with Tailscale. A server can have HTTP/S exposed to the world, but its SSH can stay behind Tailscale to enable defense in depth.
Keeping Tailscale as the only security layer will be foolish of course, but keeping the entry points hidden from general internet is a useful additional layer, if you ask me.
As a matter of principle, I like keep the number of open ports to a minimum. Let it be SSH or VPN, it doesn't matter. I have been burned enough times.