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Selfhosted
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Welp, I did it. One nice thing is that Cloudflare has an official WordPress plugin that applies recommended security settings.
I will note that WordPress does not take kindly to being setup on http localhost, then put into a Cloudflare Tunnel. It goes into a redirect hell that I wasn't able to figure out. You basically need to setup the tunnel, then run the WordPress install script from scratch.
Exporting from http localhost to your URL on Cloudflare is also not fun. The import process fails at pulling in your photos. Luckily, my blog was mostly empty, so manually re-adding the media to the posts didn't kill me.