Wish List
There are some features that I think would be very useful to a classifieds section. So far, I haven't seen them in a drupal install, but here they are:
image gallery
If you're selling something, perhaps you want to show multiple images of the item you're selling, like on ebay. My classified nodes are done in CCK, and the image field (using image_attach) is just for a single image. If you want to allow more images, I suppose you can create say 5 image fields, but then how should those images be displayed on the node so that it's pretty?
search query with filters
I haven't been using the search engine module on my drupal installations, but in terms of allowing users to generate a list of nodes according to what they're looking for, Views is superior to the search engine. What I'd be interested in seeing is a marriage of sorts where you can perform a keyword search but at the same time apply various filters (including location).


job opening - looking to hire developer
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Why not just allow multiple
Why not just allow multiple fields on your CCK imagefield?