I've lost a little bit of time to this over lunch. I've had things like TTConsole, etc. running on my ONE v2 before but I've not really ventured into it any more predominately because the network stack only works over bluetooth (in my understanding), and I sadly have little use for a bluetooth dongle on my main pc thanks to the work laptop.
If you went down the route of emulating the behaviour found in BTConsole to create a connection for an application like this, I'd imagine that you'd have the same problem in that the Windows support is iffy. I'd also imagine if you're willing to ditch the official firmware you might have a much easier time developing an application to do this, but that obviously has several drawbacks.
Unless the way in which the TomTom Home application talks to the unit (to allow you to control it) has been reversed engineered and documented (perhaps it's simply a copy of the framebuffer and input redirected over the USB, in which case bang goes that idea)?
Definately a very, very, very cool idea though and certainly one I'd love to poke at and investigate in more depth
