I've been using Caddy for at least a year now, and I host several high-traffic sites on it.* I was one of the first people to try the Let's Encrypt support when it was in Alpha. The Caddy team has been amazingly supportive and responsive during the whole process. Last week when I read this post I immediately dug out my personal credit card and donated $75. It's not much, but they add up. I hope others will too. I agree that making a paycheck out of open source is complicated and confusing. Cheers to Matt & team for trying.
* Not HN definition of "high" probably, but still, not joe's blog either.