If anyone has experience with this, I would greatly appreciate your suggestions.

I've got a client that wants a Joomla 1.5 site (or another cms) from which he would be able to:

* Sell ad space, mostly banner ads, but also within the website.
* Offer classified ads, which would be able to be sorted by zip code. The tool would have to track the size of the ad and charge accordingly.
* Have a yellow page listing service.
* The customers would be able to pay for the ads via an online payment system (not paypal).

All this would have to be integrated with membership database. There are currently over 50,000 professionals receiving a newsletter by mail, and the hope is to integrate all of it via a content management system. I'm most familiar with Joomla, but would entertain any solution, open source or not.