Wages have not kept up with the cost of living
It is difficult, but not impossible for a few, to find an affordable place to live, that is not:
-so small U may need to open the door to change your mind
-a dump
-so far away you must commute 45min to an hour each way.
The company, particularly in the Ski School, does not give new managers/supervisors enough education/training in being a manager when they are elevated from with in.
The Aspen Ski Co's IT department seems to be constantly finding new way software that makes job more difficult for the employees and the transaction time for the customers longer. (Although, I must say that last season 10/11 winter, the new ticket scanning system worked so much better than I thought it would! based on my previous experience with SkiCos implementation of computerized systems.
Interdepartment relations/cooperation tends to function poorly. One department does not know what other department is doing. Each department appears to guarding their own turf and/or competing with each other rather than working together enhance the guest experience so the Aspen Ski Co can better compete with the rest of the vacation/leisure industry.
Company/community can be a bit slow/resistant to new trends ie, snowboarding, terrain parks. (This may not be true for "Haute Couture" trends though:)
There can be an "Aspen Superiority Complex" that operates within the minds of many of the long time employees in the Ski/Ride School. It is seems to manifest in the belief that Aspen is so much better than any other ski area that there is not much that could be learned from outside our lovely little valley and that we are somehow inoculated from the troubles of the outside world. This blinds them to new ideas and potential threats.
Seasonal work