So, I got it to run!
In short, the problem was that two MS Visual C++ DLL's were missing.
MFC40.DLL
MFC40LOC.DLL
These files are freely distributable with applications built using VC++, but for whatever reason they were not installed with PSS.. or, PSS tried to install them but failed... Or... Anyway, for whatever reason, they are not there.
I found the two files on my Windows machines (one on one machine, one on another), and put them in my ~/.wine/ directory, and kazam, no problem.
But I don't have it talking to the Protea yet.. I have to work out the COM port stuff. WINE does support linux serial devices and in theory should work with a USB-serial cable, but the drivers for those can be pretty tricky so we shall see about that tomorrow