Senior Member
Join Date: May 2007
Location: Highland Park, NJ, USA
Posts: 3,798
Bikes: "Hildy", a Novara Randonee touring bike; a 16-speed Bike Friday Tikit; and a Specialized Stumpjumper frame-based built-up MTB, now serving as the kid-carrier, grocery-getter.
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mathmare, welcome to the forums. The commuting forum is indeed great for advice on fitting racks. Also, the Clydesdale/Athena sub forum is a good resource for advice on bikes for heavier riders. (Such as myself.)
You can certainly get a good bike for $500. The Trek hybrids are well-thought of, and easy to get ahold of to test-ride; Trek dealers are everywhere. Just make certain the one you buy has mounting eyelets for a rack. A used bike will get you more for your money, but at a cost of more time.
Shops: Steer clear of the ones that try to sell you racing bikes. (There are a lot of those.)
Frame size: There are height/inseam approximations available, no doubt, but nothing beats riding a bike. You'll want to try slightly larger and smaller frames anyway, so just get to a store and go!
(Also, some REI stores have the 2010 Novara Randonee on closeout now. It's overkill for your purposes--it's more suitable for carrying groceries on a trailer or a touring load on the racks--but it's a killer bike, easy to ride and amazingly comfortable. And it'll get you up those mountain hills with ease!)