Meatwad - would have a
very close look at obstacle clearance, even VFR. The statutory 1,6% requirement means jack all if you impact the terrain. That said, I'd suspect you'd be able to fly privately out of there if you follow Roaring Fork Valley.
Aspen is deffo not the place for those who live by the old "we'll just avoid obstacles visually"-track. You need a plan andsome numbers to back it up