The Subarus should get somewhat better gas mileage than you Jeep, but probably not enough to justify what it will cost you to switch. To get the EPA highway ratings you'll have to keep your speed around 55 mph. Visbility does tend to be very good with them. In the past they've gotten expensive once over 100k miles, but the 2010 and up have been very good so far aside from some reports of high oil consumption. Make sure you find the seats comfortable.
You might also try the Mazda CX-3 and CX-5. For 2016 they're offered with an Eyesight-like package, though I think only on the top trim level, and so possibly over your cap. If you can do without AWD, also check the Mazda6 sedan.
Recent VW reliability has been okay but not great for up to six years. The TDI is very efficient. With winter tires traction could be good enough in the snow. Visibility is also very good. So if you're willing to take a chance on front-wheel-drive traction, these could be a good match. One thing to be aware of: with the DSG transmission the every 40k miles fluid changes are very expensive, as much as $500. The CVT in the Subarus could also require expensive fluid changes--worth checking.
The Prius is efficient and reliable, but not great in the snow.
