When you have a simple tool you have written for yourself, that you need to be reliable and accessible but also that you don't use frequently enough that it's worth the bother of running on your own server with all of that setup and ongoing maintenance.

Security. I host personal sites on Linodes and other external servers. There are no inbound ports open to the world. Everything is accessed via Cloudflare Tunnels and locked down via their Zero Trust services. I find this useful and good, as I don't really want to have to develop my personal services to the point where I'd consider them hardened for public internet access.

Not even ssh? What happens if cloudflare goes down?

Not oc, but services like Linode often offer "console" access via a virtualized tty for VPS systems.

Having a local backup user is a viable backup path then. If you wire up pam enough you can even use MFA for local login.

You could restrict the ssh port by ip as well.

Then I log in to Linode or whatever and open a hole up in the firewall. That's easy. But Cloudflare rarely goes down, not really something I worry about.

Free bandwidth. (Also the very good sibling-answer about tunnels).

Price

Cloudflare gives me free resources. If they tomorrow reduced my blog to be available on a single region only, I'd shrug and move on with my day.

The DX is great: simple deployment, no containers, no infra to manage. I build a lot of small weekend projects that I don't want to maintain once shipped. OpenWorkers gives you the same model when you need compliance or data residency.

It takes a minute to setup for CDN usecase.