Hey dustin, i've been really racking my brain over this issue for quite sometime. It's even kept my new system out of the car for most of the winter months.
I live in New Hampshire, just above you and I feel your winter pains. Here is what I'm working on.
Creating an ultra Lite version of windows xp, that still has the functionality that my front end will need for me to be satisfied and this include the norm of DVD play back, voice recognition, MP3 and all other support compressed audio e-mail and wireless internet. (more but this is the gist nothing really new)
I'm going to store this OS (that loads my front end) on an Extreme III 1gb san disk CF card.
I will then have to take my 2.5" laptop harddrive out and put it into a USB enclosure, which would make it easily removeable. My OS will have Minlogon and EWF (among other XPe components)
My media, will come from the removeable harddrive. Here's the current issue I'm working on. My front end runs off a database, typically you would install your app with the OS. But with EWF enabled, the front end would never remember changes to the database and this can be somewhat of a hassle. ALso, if you install the app on the removeable drive I can forsee me forgetting to put it in somedays and the system would boot but with no shell and that can also be painful !!!
I'm ironing out a smart front end that will be installed with the OS but have it's database located on the removeable drive, if the removeable drive is not present then the front end will run but in a "no database" mode. Because my audio files will be located on the removeable drive it probably wouldn't be able to play mp3's but still be able to recieve weather updates, go online watch DVD's and play regular CD's or even mp3's stored on a CD.