I've been trying to build a site similar in function to craigslist in Drupal. The idea, is to make a geo-aware platform centered around bartering, instead of general classifieds or sales.
I love Drupal, but I'm struggling to get location/googlemaps integration to play with the listings and ended up using too many custom snippets I got from various folks that I can't figure out how to logically extend the site. It's basically... just a big mess now.
My client needs this on a CMS so that it's relatively simple to manage... but I don't know if anything besides drupal has the simplicity for the design and the nice back-end for the client.
Any suggestions? I'm dangerously close to the deadline and don't have the funds to outsource, so if I can't come up with a solution, I'm going to be SOL.
Why not just use taxonomy for the locations, do a one time population of the regions and be done with it. It's difficult for me to imagine that there are many places that you need actual geocoding, but any time that you do, it's hard to imagine that you'll find anything that does what you want "out of the box".
Create a static vocabulary for regions (Texas->Houston, Florida->Miami, etc ), and a vocabulary for items (Electronics, Gigs, etc) and call it a day.