Used Watchtower on my Synology for a while and it worked well. No issues in that time.

Now I’ve moved to a Nuc and am more experienced with Docker and understand a lot more of it but by no means am a professional by any means, I would say that I wouldn’t use Watchtower. I can definitely see it messing a config up and prefer not to deal with the headache of troubleshooting something without knowing it was an auto update. If I had the time, I may tag the apps I’m happy to auto-update but for now I prefer to have the higher availability.

I’m living in the EU myself and I’m also quite weary of just downloading, but amongst friends and myself, we just use usenet and sometimes torrents with VPN and as long as we are careful, downloading generally isn’t an issue.

Of course, that does mean you have to pay for a service first such as VPN, and maybe that’s not something you are willing to stomach. This is definitely feasible. Your method might work but involves a lot of work to get it going and anything could take out that workflow. Downloading onto your local machine is generally going to be fine.

Look into usenet, vpn torrents and seedboxes.

Can you let us know why you want to have such a seemingly convoluted method of downloading such media files?

Why not download locally and directly onto your computer or server?

Assuming you are wanting to sail the high seas but think of the Pi in another country as a method to get around restrictions, look into the following: usenet, vpn torrents, seedboxes.