Hi Ryberg:
Garmin stuff I am somewhat familiar with, but the Apple OS and Virtual PC - geez, I haven't used that since System 6.3 back in the early 90's. I was a developer for Apple at one time, but that was in the 80's... before the old King died.
Personally, I think you are 'hosed' if you want to load your datachip or GPSR from MapSource running under emulation on the Apple OS. My guess is that the application (MapSource.exe) would probably run pretty well by itself under emulation, but the problem of data input / output you have encountered is close to insurmountable. For sure, Garmin has no plans to release a Mac OS version of MapSource.
If I recall correctly, the GPS V uses a serial port connection to communicate with the computer, not a USB port. The USB port is only used by the newer SP 26xx series for direct communication with the GPSR, or for plugging in the chip loader that is used with the StreetPilot series (SP, SP ColourMap, SP III), and other GPSR's such as the 176 that use data chips. Have you tried communicating with your GPS V via COM 1 and then the Serial Port? (Not sure if the PowerBooks even have a serial port or not).
If all else fails, you can back up your unlock codes for the CitySelect cartographic software onto a floppy disk (they only occupy 1k or so), then take that floppy to someone else who is running the same version of CitySelect as you have. Then you can upload map segments from their machine (a Wintel machine) to your GPS V.
FWIW, it's a useful trick to always travel with a floppy that has your unlock codes on it. That way, if you come across another computer (someone else's) with the same maps on it, you can install your unlocks, then upload from their machine. You don't need to worry about removing the unlocks later, they are only good for your GPSR anyway. Might be worthwhile to put your name in the comments field, though, just so the other person can figure out what's what in the future.
PanEuropean