Let me state for the record that I live in Grand Lake, so I'm biased.
Many people think of Grand Lake as a 'Renter's Area', and that is true to a certain extent. We do have a fairly large rental fleet here. However, Grand Lake's riding area is quite large and diverse. Hill Climbing, Well-Groomed Trails, Trees/Off-Trail, Meadows, it's all here, you just have to know where to look. We're not as large and open as Steamboat/Rabbit Ears, but we are closer to the big 'D' by over an hour. It's also legal to ride your sled on the streets in town as long as you obey all the traffic laws (speed limits and stop signs).
We have a large amount of lodging for a small town, including hotels, cabins, condos, and homes (some very large), any of which can be had for a fair price in the Winter time (Summer is our busy season!).
And, to cap it all off, Grand Lake has FANTASTIC early season snow right now. I rode this morning (Sat) and there was at least a fresh foot up on Gravel Mtn. Best early season snow I've seen here in years.
Hope this helps. Let me know if you have any other questions.