Does anyone know if I could just run the streaming server on my own stuff but then set it up with Cloudflare's proxy dns? That way I can run it only when I want to and skip the $5 without doxing my IP.

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Yes, you can, but I couldn't find a nice and easy HLS server to self-host.

You can probably also use https://vida.live/.

I use liquidsoap. The learning curve is steep though.