Hi,
> As such, I'm looking for a little advice on debugging issues when apps
> don't work (yes, I've read what's on winehq.)  I have the application
> KeePass (keepass.sourceforge.net) which installs just fine.  When I go to
> run it, it just drops me right back to the prompt.
Pardon my ignorance, but why don't you use the Linux version instead? 
http://keepass.sourceforge.net/download.php lists a Linux port.

If you have the necessary tools to compile keepass, you can build the Win32 
version from source and put a few debugging printfs into it, to see where it 
stops. This could shorten the debug time greatly. (Of course this doesn't 
work for apps where the source isn't available)

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