Yes, turns out you are correct about that.
I also corrected by virtual hosts for 80 and 443.
If I go and pull up
http://owncloud.leeburch.com/.well-known/acme-challenge/iamhere
it works fine (from an external network)
Yet 9/10 times when I run certbot I still am getting:
http://owncloud.leeburch.com/.well-known/acme-challenge/S-JDPCRSIKZRbDubFpcHyKVFq5q-gTSBKgpLbkXHmao:
Timeout during connect (likely firewall problem)
Yet 1/10 times or so, it actually works. with no config change on my part.
I even see the request from the certbot servers and see that I am serving a 200 return code on the request, yet the certbot still usually reports timeout.
I am wondering, is this a problem on my end or that I can pull up files in the challenge directory and that sometimes certbot can too mean the problem is happening elsewhere?