I think this classifieds script will be able to do everything I want and the support so far seems to be solid.
My biggest complaint right now is that it doesn't look nearly as good as the demo once installed on my site with my template. Some of the forms even seem to be broken on my site. I'm going to try and style it to match my template which I think will fix everything.
Not a complete turn-key solution, but it will probably get you 90% there.