There may be other problems, but this will be a definite blocker.
…which is your problem. Let’s Encrypt will only issue five certs for a given set of FQDNs within a week. You exhausted that limit within 45 minutes. Once you did that, any further attempt at installation was guaranteed to fail.
I did the normal installation the first time, an error occurred.
I did the second installation on digitalocean with one click, the same error happened.
It hasn’t worked since the first try.
I have been running discourse with cloudflare (hosted on vultr) for almost an year now. If You have a budget, maybe consider hiring someone to do it for you if you can’t figure out the exact problem. Feel free to post in #marketplace
That means there’s something funky with your Cloudflare setup. If Cloudflare is running in DNS-only mode, it should function identically to any other DNS provider, Google included. If it doesn’t, that’s a Cloudflare bug, and you’ll need to reach out to their support team.
…and if it’s a Cloudflare bug, it isn’t a universal one–I personally manage two Discourse sites that are using Cloudflare DNS, and I’m pretty sure I’m not the only one.