Unless I had multiple users who'd need to login of course, but then Tailscale suddenly become a paid product, and I'd probably add another instance as a bastion host at that point.
I guess my point is: Make sure the software you already have is configured the right way before adding more software on top.
But the ordering before that seem very reasonable. Although Wireguard is a soft alternative to changing default port, so it might be worth doing that.
On a slight tangent, I’ve never really bought into changing SSH port from default. I’d say the convenience of not having config/extra port specification is worth having it on a well known port, but that’s just my personal philosophy. I feel like for my low traffic things, just having strong SSH key and auto-updates is good enough.
But I guess this is partly because I tend to look at logs a lot less than I SSH into my server.
Couldn't agree more!
[0]: https://tailscale.com/
[1]: https://tailscale.com/blog/how-nat-traversal-works/