Fun first car

Consumers Reports likes:
Acura TL (2006), Acura TSX (2006), Hyundai Sonata (2007-09), Mazda6 (2009)

Subaru fan here, my bias would Impreza, great in snow. 2006 or older might be in that price range.

The older cars get, the less reliable they get.

For safe handling and braking in the winter, I'd set aside $800 or so for a second set of wheels (steel is fine) with good winter tires.

My personal preference is for compacts. They might not be as powerful as a midsize with a V6, but they're much more agile and fun in typical daily driving.

For reliability, newer is always better. One value buy I often recommend is the 2008-2011 Ford Focus in SES (sport) trim. In this trim (denoted by dark multi-spoke alloy wheels) the suspension tuning is European. Not the most stylish cars, but they don't look bad in blue.

The Acura TSX recommended above is a very nice car, but you might have to get an old one with many miles to stay within your price limit. Same with a Subaru Impreza. Subarus tend to be reliable early on, but can get expensive to maintain once over 160,000 km.