Direct flights to Aspen are sweet for those of you who live in major metro areas. I might pay the extra cash for that too but it would be hard to turn down the directs to Denver at $125 RT (frontier and spirit, $200 for AA)
20% of trips (2 flights * 10% of flights) is a high rate of hassle and I'm pretty sure they wont refund the $425 price difference
Most of my trips are solo four day ones over a weekend. Catch the 5:55 Thursday night, land in time for a late dinner and fly back 3:15 Monday afternoon.
Don't need a rental and I can take the free bus into town. If a flight gets cancelled when I'm in Aspen, great! I'll stay until I'm confirmed out.
It's worth the premium to me.
Most of the legacy airline flights to Denver are more like $300+ for decent times. But if you have a bunch of people, it adds up and Denver is an option.
I use Southwest a lot because I can book a bunch of possible flights, use the ones when conditions are good and the miles from the unused ones go back into my bank.
I currently have five booked up till 2/16/15 and then I'll book more when they have the sale for late season.
I've been dicked by both Frontier and Spirit. I'll will leave the low cost/no service, smoke and mirrors for others and hope not to be stuck in the airport.
The trouble with the low cost guys, the equipment is spread so thin, if they have a mechanical, your hosed.