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.
Couldn't agree more!
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.