The main issue is and has long been staffing. Dodge Ridge is far from any major population centers so commutes are long, and sometimes dangerous, and the pay is not competitive with other local businesses. Upper management insists that the poor pay isn't a problem because of the benefits, but when the only benefits are a free pass and free rentals and you don't have any free time to use them due to severe understaffing, they don't count for much. This often leads to less than ideal candidates being given jobs that they aren't suited for, and a less than ideal experience for customers (a lift operator not stopping the lift on time because he's worked for 17 days straight, alone at his post, an instructor being given huge (10+ students) lessons despite having only first strapped on skis the day before, or Guest Services continuing to sell rentals even when totally sold out)
Another issue is top-down micromanaging. Even though most of the department managers are highly experienced and very competent, they are generally not given the power to make decisions about even basic things like scheduling and approving overtime.
Outdated and run down equipment is another problem. The newest chairlift at Dodge is Chair 8, at 22 years old, while Chairs 1, 2, 4, 5 and 6 were built in the 1950s. As you might expect, all of these lifts have their various problems. (It should be noted that these problems do not make these lifts unsafe, as in almost every situation the lift will shut down automatically in the event of a brake or power failure, but stoppages and closures certainly don't help with customer experience) The Lift Maintenance team are very proficient, but they're not superheroes, and there is a limit to what a group of five people can do. Management has been claiming for several years that they plan to replace 1 and 2 with a brand new high speed 6-pack chairlift but there doesn't seem to be any real merit to these claims.
I hope I have provided some insight into why things are the way they are