Hi Chris,
There were some fixes to incorrect configuration paths in the rpm/debian distributions that was fixed in 1.5.2 and 1.5.3. A problem was that the installed config file location was not correctly set (part of that fix was the diff that you noticed in /etc/rundeck/profile). This might be your problem with the gui setting.
(the "NO JSP Support" warning is not related I believe)
How does rundeck fail to start if you use the .location value?
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Seems like a configuration issue. If you want to send me your config file (or most of it) directly, I can take a look.