A few random thoughts
@coskigirl: Your CX-5 will make a fantastic used vehicle for someone. Why not you! Having been shopping for a used vehicle recently, it's fantastic when you find one coming off lease. It's especially nice for you since you know the history and where it's been. You can probably buy a factory extended warranty and make it the same as certified used, saving a ton of money over new.
As for a hybrid, I don't think they are the greatest for I-70 skiing duty, especially a big one like the Highlander with the 2.5 four-cylinder. If the vehicle is loaded, that pour little engine has a lot of work to do climbing the passes after the battery is depleted. I'm sure it can do it, but I wouldn't want to own it past 100,000 miles if it had a rough life of I-70 duty.
I'd consider in your shoes to keep the CX-5 and also buy a $10K Prius. You could put most of your miles on the Prius and only use CX-5 when you need space, power, or snow tires. The Prius would be fine for Eldora trips when the weather is decent. Doing the math on the depreciation of a new vehicle, you can often own a quiver of used vehicles for the same cost, each better suited to a specific purpose.
Yes, it sounds like all the Toyota body on frame SUV's and the trucks they are based on will have a hybrid option in the next few years. I think (hope) a hybrid 4runner powerplant will probably be better suited for I-70 duty than the car-based SUV's. I also doubt it will get anywhere near the milage at the Highlander. We'll see, but I'm hopeful Toyota will get the powertrains that will be used for the next decade right. I do think I'd rather have a used old school 4runner (or GX!) and a Prius over a new hybrid 4runner, and combined the two used vehicles would likely have a much lower footprint.