I've spent too many hours googling this stuff without a solution in sight that I'm able to understand.

I am moderately new to selfhosting, especially the networking aspect. To put it simply, all I want is to be able to access my services through Tailscale by using subdomain.mydomain.com.

I have gotten so far to point my domain to my Tailscale IP (using Cloudflare's DNS), so that I don't have to copy paste the Tailscale IP, but that means I still have to type in the ports to the services. Between the posts saying Tailscale can handle this, to the ones saying Synology can do it, and the remaining posts saying to use a reverse proxy (and the ones saying reverse proxy are a bad idea because of Synology stuff) I am now very lost. The terminology is exhausting and everyone is already so knowledgeable that they skip the basic steps and go straight to complex, short answers.

I'd like to keep using Tailscale, as I don't want to deal with security issues and SSL certificates and all that, and if possible I'd like to avoid using a reverse proxy such as npm or Caddy if there's a built in Tailscale/Synology solution that works.

To me more services just means more stuff that can break, and I really just want this stuff to work without fiddling with it.

Thanks for any help you can provide

I am at my wits end with this and kindly ask for assistance.

I cannot for the life of me decide on how to set up my music library for the foreseeable future:

• I started out having my library on my local pc, managed by MediaMonkey
• As I bought a NAS, I moved my library to it and used Navidrome to stream it to an android app (Synfonium)
• This meant that I'd lose the MediaMonkey management, but I thought for now I'd just manually transfer new songs/playlists over to the NAS when needed
• As I started streaming with Navidrome, I noticed that the speeds were really bad and music often buffered (no idea why, Jellyfin works fine), so I cached all the songs offline
• This made me think that I don't even need Navidrome since at that point I could just copy the music files to my phone if they're gonna be offline anyway, but then I don't have a backup on the NAS

And now I'm kinda lost, unsure what the best way to handle this is. I'd like to keep MediaMonkey in the flow for library and playlist management, and streaming is pretty cool for those times where I'm listening on other devices. However, having the music on my NAS just seems to create an extra middleman. What's most important to me is a smooth mobile experience, with a good UI and no interruptions, as that is where I listen to music 95% of the time.

How do you do it ? Any suggestions for how to future proof my setup without too much of a hassle (still kinda new to all this stuff)? For reference I don't have a huge music library, maybe a few dozen GB, so it still fits easily on my phone.

Sorry if this was too long or doesn't fit the subreddit, but I hope someone can enlighten me.

And if so, would they get more prison time / a larger fine?