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So is Tailscale the first thing I should set up next? or do I figure out the Arr stack and other software first and then set up Tailscale?
If tailscale is your preferred method to access your network from outside your home it's one of the most important parts of your setup, in terms of both security and functionality.
Luckily, overlay VPNs like tailscale are pretty easy to set up without glaring security problems, but you definitely want to triple-check you aren't messing things up. The thing is, you don't know what you don't know, so you might not realize if you make a mistake. But like I said, it's pretty hard with those types of setups.
To actually answer your question though, I recommend you get one or two containers working locally and then figure out how to access them from your tailnet before you dive in and set up your entire stack. Docker adds another layer of complexity when it comes to accessing things so I recommend you get it right and then deploy and test each container individually.
Don't set up 10 containers and then try to see if they all work, go steadily and deliberately, checking to make sure each works, and then snapshot your functional setup before you start using it heavily.
Don't forget to plan for backups and updates.
thank you! I'll try to set up a shopping list program first then to test it. If anyone has any to recommend, I'm willing to hear suggestions!
I don't actually use the arr stack, but if you set up Tailscale it won't hurt anything else by being set up. I just know that it's pretty straightforward to use, so I thought I'd throw in a good word for it.