1-Your button definition is missing the last parameter
2-You have a total of 3 quotes in the definition (you should always have an even number)
3-You >seem< to have a space in front of the path name of the command to execute.
4-You are correct, as long as the pathname is valid, it should execute the application even if the window title is wrong.
This is what I would try as the load command:
"LOAD;TOMTOM.SKIN;LCDDisplay;C:\Program Files\Microsoft\Device Emulator 2.0 Preview\DeviceEmulator.exe|/s C:\pocketpc.dess /video 800x600x16 /nosecurityprompt;LCDDisplay"