TL;DR: My updated golf1052.conf
About a month ago I decided to replace nginx with Caddy. I ranted about it here. I finally remembered that it's been more than a week since I failed at setting up https on my site. Also I read that you are now allowed up to 20 certificates per domain per week. So I updated my .conf file. How did I fix this issue?
2016/03/12 16:51:50 configuration error: Cannot multiplex golf1052.com:443 (HTTP) and blog.golf1052.com:443 (HTTPS) on same address. I removed https from my tls off blocks. Can't believe I didn't realize that earlier. Also Caddy claims to redirect http -> https if it can. For some reason it wasn't working for me so I added a manual redirect block.
I don't really have any additional thoughts about Caddy. I don't need to touch it that often if ever just like nginx and editing the config is way less scary than editing my old nginx config so I guess I would give Caddy a cautious 👌🏾.