I've been playing with Bobcat since the day it was released and I'm not finding it a particularly helpful program... starting with that MapConversion process.
I am using Parallels, and on my first pass, it filled up my drive. I had what should have been plenty of space, but first it creates this .gmapi file, which it then zipped using .tgz. Temporarily nearly trebling the amount of space used for the maps.
Once it's moved over to the Mac side (In my case not necessary because of shared drives), MapInstaller/Bobcat couldn't read the .tgz file. I had to manually extract it before it would read it. (Talk about wasting a lot of time to accomplish nothing!) Now I do have three copies of the maps. Then in imports it into your ~\library, making a fourth copy!
Yes, you can delete the extras, but talk about inefficient.
One thing I noticed about some (all?) of the map products, the DVDs contain data in .CAB format, which is microsoft's format. It's possible that a licensing agreement may prevent using that format directly on non-Windows OSes. The whole MapSource installer system is a bit wacky anyway, it's possible garmin might be moving away from that to the when "all products will be Mac compatible by year end."
Another complaint: Bobcat seems to turn my GPS off every time I try to transfer data to it. Click Send or Receive, GPS turns off instantly.