Oh, you must ride more than the parking lot!

My LBS lets me take bikes out for 10-15 mile test rides. It's hard to know with just a parking lot ride. Half an hour or more is good, I think.

Steel: I have a Surly Cross Check ($900). Surly Long Haul Truckers are nifty ($950) Jamis Aurora are sweet and smooth ($850). Trek 520 are classic, but more than $1000. Really, if you can find used steel it will be cheaper than new. There are enough steel nuts on TE that you can get plenty of guidance as you search through steel used bikes on Ebay or Craigs.