I am looking at driving vs car rentals to attend the Aspen Gathering. If I fly, I figure I'll rent a car for a few days to explore the area and maybe ski one or two other resorts, either before or after the Gathering week. While it cost more to fly into Aspen/Pitkin, it seems to cost less to pick up a rental car there and drop off in Denver than it does to pick up a rental car in Denver and drop it off at Aspen a few days later.
I booked a midsize SUV at DIA for the Gathering via Alamo Insiders. $446 for 7 days with accelerated check-in. I'm eligible for Skip the Counter and I'll do that as well. It would seem that I'm in decent shape for the rental and yet I can't help having this feeling that I need a back up plan.