Craig,
could you please set the controller log level to information as this might give us some hints what is going on, you could find the setting in > controller > logs > logs configuration > wireless controller log level.
Then connect the remote AP again ... or reboot the AP via remote and let me know whether you get log messages in the log and which one.
The normal logs for a AP that connect to the controller will look like that...
I think in your case that last one "Blacklist successfully sent..." is missing.
In that case it's a MTU problem = the AP can't discover the MTU on the VPN link.
Just set it in the static AP config to MTU=1300 - if the VPN uses a smaller value try it with a even smaller MTU.
For even more detail what is going on you'd ssh to the AP and go in the /tmp/log directory.
Then do a "tail -f ap.log" to see what the AP is trying to do.
Ron