I have long tested the Street Atlas software in hopes that it would work with Wine. The old versions (circa 1999 or so) would run, but with slanted text all over the map. When DeLorme adopted a new interface design (with the "Road Warrior Edition", circa 2000), it broke all the Wine stuff, and I never got it to work correctly with Wine (all the panels just displayed "No component" or something similar).
I just ordered the new 2004 edition, and it works quite beautifully. There are a few bugs (see "Known Issues" section where I've posted them), but it runs!
I will test out GPS and the text-to-speech features soon. I only have a serial cable GPS, so I cannot test it with USB or Bluetooth, but I suspect those have less a chance of succeeding than serial cable.