Pros: Skiable acerage, value, lift system
Cons: Sub-par layout, elevation, access to I-70
Winter Park has lots of terrain to offer, from open green groomers to gnarly avalanche-prone chutes. The snow is very dry. There is ample tree-skiing to be had; the possibilities are endless. However, one should be prepared to ski alot of bumps (especially if they go over to the "Mary Jane trail complex").
Most of its lifts are high-speed detachables, allowing more time to be spent skiing. However, the layout is confusing (especially to new visitors) and it is difficult to get from some parts of the mountain to other parts. One of the more desirable spots to ski (the Vasquez Cirque) is often closed and requires a 30 minute hike at 12,000 feet to access. This brings up the point that like many Colorado resorts, the high elevation of the resort (with a base at 9,000 ft) means that many low-elevation dwellers will have an especially hard time acclimating to the environment.
One particularly troublesome issue is that quick access to Denver relies on the Berthoud Pass being open. If it is closed (which it often is due to storms, and at short notice), a 4 hour drive back through Summit County is required to get to the Denver area.
Crowds are rarely an issue, due to the lift capacity and the size of the resort (with multiple "trail complexes" that could pass as resorts themselves).
Nightlife and dining are fairly limited (compared to other resort areas).