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If the biggest thing is getting through the Jersey Winter, I'd suggest considering a 4WD sedan or wagon.
You could get the similarly priced Subaru 2.5TS Sport Wagon with a nice sound system, 5-speed transmission, Fog Lights (useful for bad weather,) a cargo bin or net to give you similar carrying capacity to the Jeep, HEPA filtration system if you have allergies like me, and the price would come to just over 20k. The fuel economy would be 21/28 with the 5-speed. Jeep's interactive website wouldn't load for me, so I couldn't get the fuel economy specs to compare.
Compared to between 18 and 19k base price for the Liberty Sport, and judging by my experience with Subaru, I would consider it as an alternative. If you wanted to go a few grand higher, you could go for a nice, sporty WRX, but it's really up to your personal taste in cars and your budget.
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