I don't know what the compatibility is with the Xbone controller on the PC just yet, but it is a very nice controller. I was pleasantly surprised at the new triggers, and their feedback. It's a great sensation playing racing games and FPS's.
Google Maps doesn't have an offline mode yet. Supposed to get it soon.
It currently has cached routes so you can still use it as a pseudo GPS but it's only for those specific trips.
I'm actually surprised to hear that you've having problems getting the 32bit programs working in 7. I've never had a problem with anything 32 bit. Maybe I'm just having good luck?
Are there newer versions of the software? It just seems weird to go backwards instead of forwards.