You're already ahead of the pack. You've identified a (somewhat) firm budget, realized that as a complete novice to avoid an online purchase, decided to stick with what is available at the various LBSs, and willing to listen to advice.

BTW- 'Cycling Environment/Conditions' basically means surface/weather conditions, hills (big/little/none), traffic density/speeds. Just state you'll be riding in NYC and most people should draw their own conclusion as to your enviroment. Also, IGH stands for Internally Geared Hub.

If you got the time, you might want to check out the glossary of terms on Sheldon's site.