A couple thoughts:
You can fit an SUV in a garage with a Yakima LoPro box. Our MDX fits everywhere. It's nice to be able to leave the box on and not worry about parking structures, etc.
Maybe at some point (after the mountain home!) consider adding a third, cheap, used off-road capable vehicle. The more vehicles in the quiver the better, right!
Good ski vehicles, like your Outback or our MDX, fill a different spot in the quiver than an off-road vehicle, IMO. Paying for the gas and wear and tear on an off-road capable vehicle for front range skiing and commuting is unnecessary. It's really the summer excursions when you need the off-road capabilities. In the winter you really just need snow tires. The first year depreciation on a new Grand Cherokee will buy you a decent used off-road vehicle to add to your quiver.
Not necessarily! I usually don't bother taking my Tundra to Moab, as I'll mountain bike from the trailheads and get around even faster, and save a bunch on gas. A real 4x4 is very useful hiking, camping and backpacking, though. I'd probably not bother with an off-road capable vehicle if I just mountain biked, as I'm not really into off-roading for its own sake.
Edited by tball - 10/28/14 at 12:42pm