$1500 is a lot, but if you can swing it, I'd definitely go to T-ride. A Winter Park trip is just easier to put together if you want to do it in the future. T-ride is gonna be more expensive and a bit more of a pain in the ass since it isn't convenient to the Front Range.
I still haven't ridden at T-ride, but it's a stunningly beautiful area. One of my favorite parts of Colorado.