be brave, go the shops in your town, whatever the reviews say, and test ride them. Tell them the same thing you're specifying here, under $500 etc.

That is the beginning, not a bunch of strangers recomendations of shops. Find out what they offer for servicing in the first few months of ownership. Learn how to recognize sufficient air pressure in the tires. Some shops forget to put air in the tire, some might put the same amount of pressure for a 120lb person as a 220lb person. Your impression of the ride can be affected by tire pressure. If a shop gives you a bike to ride and the brakes squeal horribly mention it to them, if they blow off your impression, "oh that's easily fixed" or can't correct it that's a clue how they will service your bike after you buy it.

Personally if I was looking for a bike with some kind of upright bars I'd prefer old fashioned 3spd/swept back bars and not straight/mtn bike type bars. The former put your hands/wrist in a natural position while straight/mtn bike bars put them in a torqued in position that's pretty poor for resting weight on hands.