Firstly, thanks for all the replies
secondly, I am an airplane pilot, just not the "commercial pilot" aka airline pilot. Believe it or not, lots of us have no desire to be airline pilots and make freight/charter/corporate a career. I personally do freight. It is sometimes more lucrative and personally always more rewarding than airline jobs. But I digress.
At any rate, I don't plan on living in Minneapolis or anything crazy like that. I just want to be able to move bases or companies at a whim. Say I am in Austin, TX but the San Diego, or Las vegas base opens up, I can be ready to move in less than a day. That's the kind of flexibility I want/need.
In regards to the whole TT/Truck combo, I don't own a vehicle (at this current job I'm home less than 4 weeks a year, no need for a car) and I really don't see myself buying anything bigger than a ford ranger, so as long as something can be had for that size that would work for me.
Again, I don't WANT to be in minneapolis in the winter, but there is a lot of activity in Omaha, Sioux Falls, Portland, Seattle, Sanfran, PA, Texas and so on so I may end up in a place that gets a good bit of snow or what have you.
This is all in the preliminary state, just thinking at the moment.