Help me make a decision....

Regarding your re-entry in the fold and your locale, give some thought to riding position comfort and control. A more upright riding position might be more to your liking after about 1/2 hour in the saddle of bikes like the Buell "Long". A windshield or 1/2 fairing of some sort is another item that many riders overlook in a daily rider. Naked's are great in the nice weather, so long as you can deal with bugs/road debris/and rain, but for a daily rider, the value of a shield is invaluable, especially one that is easily detached. Cost is, of course, very relevant, as well. There's not that many perfect options for you in the under $10K category and it appears your already thinking about the V-Strom - a good choice, especially because it has EFI, fairing, and reasonably upright seating. Lastly, if you plan to do a lot of 2-up with luggage, you'll want to test ride with your significant other to see how satisfied you're going to be with power/torque performance of the machines your considering in the graded mountainous environment your in. But, in the final analysis, you've got to consider more that just the practical side - you've got to love or at least like the aesthetics (the look, the sound, the feel) of the machine. Do it!!!! & good luck!