We just got back from a week in Winter Park and absolutely loved every minute of it! We've been to five other CO resorts in the past (Breck, Vail, Steamboat, Aspen, and Copper), and for skiing, we loved WP the best! We are intermediate skiers, and found plenty of challenging runs, including some of the greens off High Lonesome Express, and Olympia. Some folks complain about the flats, but once you know your way around the mountain, you can get through them without much trouble.
Speaking of getting around the mountain, we found this the easiest and most hassle-free of any place we've been. It was really straightforward and simple to go from WP to Vasquez Ridge, and over to Mary Jane. We were able to ski plenty of runs each day on all three peaks. The best feature by far is the addition of the Panoramic Express lift to Parsenn Bowl. What a treat! There are runs for everyone up there, the view is fantastic, and we just loved skiing the glades. Wow!
We stayed at the Vintage Hotel, which was nice, and will be even better with planned upgrades. I thought access to the Base from there would be a hassle, but using the ample shuttle busses was easy and efficient. Getting into town was also easy, using the WP shuttle bus, or the Vintage Hotel van. Some folks may not like the lack of shopping and dining choices, but we found good variety and quality in what was there. Besides, if you've had a challenging day on the slopes, all you really need is a good hot tub (which The Vintage has, along with a great heated pool), and a good hot meal, which is easy to find.
There is plenty of new construction and enhancements taking place all over WP, and they should make the place an even better ski resort destination. We WILL be back to Winter Park!