@cmb:
With it bound to 443, do you have your GUI bound to something other than 443? That might be one reason.
I'm guessing though it's the issue where OpenVPN writes out the wrong PID in its PID file. What's in your /var/etc/openvpn/serverX.pid file and what is the actual PID of OpenVPN instance that's running? where serverX probably == server1, but could be some other number depending on how many you have and have had in the past.
I switched the webgui port to 1234 before I created the OpenVPN service. It works fine now since I rebooted it and was quickly able to get back an IP from DHCP.
It's weird how it got into that state… The openvpn daemon was definitely running (even though it was reported stopped) and I was able to vpn in from the internet once I got an IP.
The pid file explanation makes sense. I'll try it again in a few days so I can get it in that state again and report back. Thanks for your insight.