Sounds like a different solution is in order (i.e., something that doesn't require you to carry 4-6 pairs of skis inside). It does indeed sound like a PITA, and not too safe, either.
The current premium price for diesel fuel is not helpful. It lengthens your payback period for the diesel option to something like forever.
VW has also had reliability issues for a number of years. (Your VW may be perfect, but statistically, over a larger sample size...)
The VW Alltrack is indeed attractive. It has a nice, if somewhat bland, appearance. It undoubtedly drives like a proper German car, as do most Volkswagens. But it has several factors working against it. I hope VW can address those problems. If they don't, other solutions will continue to be more attractive for many of us.