Tailscale never appears as an update in the macOS App Store

I’ve experienced the same. I think there might be a bug related to updating running VPN apps. The Apple review process also adds an indeterminate amount of time. For this reason I switched to installing via the standalone binary at https://pkgs.tailscale.com/stable/#macos.

That’s not perfect either though. For some reason the standalone build is still at 1.30.0. And really you’re still manually checking for updates either way.