Which cases? Tailscale has eliminated all my fears I had about self hosting and I've been using it a ton. The only issue I've run in to has been a single service (Withings) that uses a web hook to trigger updates for my sleep mat. Their server isn't on my tablet so I would need to expose atleast one service to the wider Internet.
I'm talking specifically about Tailscale Funnel which gives ingress access to services on the tailnet from outside (ie. on the general internet). Any case that doesn't use TLS for a transport won't work. SSH being a notable one, but I can think of several others.
How does tailscale help with securely self-hosting from home? I have it setup to interface securely with my PCs across networks (like at my inlaws), but not sure how it helps if i were to expose something to the world.
As a Cloudflare Tunnels user who only recently discovered Tailscale - just go with Tailscale straight off the bat. It's magic, and smooth as butter.