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Hi there - in the price range you are looking at, cool is going to be subjective. Fuel economy - a little easier. Great bang for the buck - Toyota Corolla. If you want something a little cooler, but with reasonable operating costs - Ford Ranger pick-up. I've been partial to the 4 wd models, but there will be some penalty in fuel economy. A 2wd truck is crummy in the snow unless you have some sandbags in the back and a set of snow tires. A Subaru would also be a decent choice, but service records are important, and models in the mid 2000's were known for head gasket issues, which would blow up your budget in a hurry
If your credit didn't get nuked in the divorce, consider a new Ford Focus. Not sure about the US, but in Canada, leasing is back. Look for a 2 year term if possible, low cash down. Don't go for a long lease - too expensive. Great cars, cost effective, comes with a warranty. Excellent fuel economy. Pretty cool
Hope that helps! Best of luck with your new life and new car! Canuck