Re: Why not use built-in wordpress functions for image handling?
I'm gonna use Gravity Forms for letting people post classifieds. This is a brand new highly intuitive contact form plugin that let's people write posts and add images to it. They don't tweak the WordPress core in any way.
Still love ClassiPress though... although I think it would be much better if it would be more of a framework like Theme Hybrid, Thematic, Carrington, etc. Already I made a bunch of customizations to ClassiPress which I probably have forgotten about by the time a new version of ClassiPress is there.