Main problem, in my opinion, is that most solutions are airport-centric. Say you want to Ski in Alta UT. You can't typically book travel from NYC to Alta, you have to specify "from" JFK/LGA (or NYC) to "SLC", assuming you know exactly where you are going, what the best airport is to fly to etc.
Some let you select "ski" destinations (as Kayak Explore does), so it may send you to SLC (Salt Lake City), show you weather for Salt Lake City, then try to up-sell you on a hotel in Salt Lake City (or maybe Sandy UT).
Mine's is destination centric. Where you fly to, where you check the weather, where you ski, and where you book your hotel (or even buy lift tickets from) are not necessarily the same "place". Make sense?