I'm sure there's a simple solution to this, but I've found that running the EQ executable from any kind of shortcut or terminal prompt results in the error Boolean described.
My fix for this that has always worked is to target the executable directly from the folder where EQ is installed in the dosdevices/C:/ProgramFiles/Sony area. When run from inside the folder with all the gamefiles EQ seems to work fine.
Also, consider using
Q4Wine if PlayonLinux is giving hassle. It's my go-to Wine GUI for running Windows executables.
Ubuntu 12.04 here, I know i'm way behind the times but it's so stable for everything I use it for I don't wanna mess with it =p