I think they may have dropped the feature but I distinctly remember being disappointed in the feature that it wouldn’t download MP3s to your server so I’m pretty sure it existed at one point.

I think a lot of people use Tailscale and add their external clients to a dedicated tailnet. How are you hosting Plex without opening any ports though?

Honestly the writing’s been on the wall for Plex for a while now. I think it was when they introduced podcasts or news or something that it first became clear to me that Plex was trying to grow beyond a software company for self-hosters and prepare themselves for an IPO or something. I still use it simply because their client availability is second-to-none and I’ve got a bunch of people signed up already, but I’ve already made my peace that the “Plex getting shittier” line and the “Jellyfin getting better” line are getting closer and closer to crossing each other.

This is true, but I don’t know if you’d be counted as a seeder on that list though if you don’t have the full torrent.

I’m personally a big fan of OpenAudible. It’s not free, but it’s not crazy expensive and it does all the work for you. You sign into your Audible account in the app, it will pull your library, download each book, decrypt it, and convert it to the format of your choice (I usually do M4B). I’ve been using it for years and it makes downloading your Audible library in an ongoing basis a breeze.

I came here to say exactly this - WireGuard is great and easy to set up, but it gets harder as you add more people, especially less technical ones, as getting them to make keys and move them around etc becomes a headache. Tailscale also minimizes the role of the central server, so if your box goes down the VPN can still function. Tailscale can also do some neat stuff with DNS that’s pretty nifty.

I only have messed with it a bit, but it does require a SMTP server because it relies on sending email for account setup.

For that number of disks, I would just buy a case that holds the number of disks you want and build a computer in that case; either move your existing home lab into that case or setup a new one and export the storage over the network.