HELP: Which plugins? User save which categories to see + ad/click management?

Hi guys, I really hope someone here can help me out with some good suggestions on which plugins to use/how to combine...

I have a potential client approaching me with some very specific wishes for functions and display for a kind of advertising site.
As I'm not a developer (can copy paste into functions.php though :wink: I need to be able to combine plugins for this.

Although I love WPMUdev-plugins, it does not necessarily need to be a WPMUdev solution, but you guys here usually rock, and since I've searched the net for hours without actually finding a specific solution, I now put my hopes that someone here can come up with some valid suggestions.

If useful, I already have access to non-wpmu plugins like Types/Views, Gravity forms etc. and suggestions can be of other paid plugins also, as long as they play nicely and will allow me to create the site as specified.

For now, here's what I need (more might come though):

Basically it's an ad site (no other content but ads, somewhat a' la' groupon, where each ad has it's own post with images, price-tag, a short description, tags, categories it belongs to etc.), but each with a link to a specific (pr. ad) off-site webpage, where people can then buy or get additional info.
The advertisers then pay pr. click on the link.

1/
On their profile page, Registered Users have to be able to choose which ad-categories that are relevant for them to see, AND be able to save those preferences.
(so that initially they will only be served/view ads of those chosen categories, BUT they should still be able to search the site for other type/specific category ads if needed - I suppose that tags are sufficient for this last part).

2/
Either a full-on ad-plugin (with possibility of link, custom fields, text, images etc.) that also registers/counts how many times the link on each ad has been clicked
- or a combination of more plugins/custom posts types etc., that together adds that function. those ad-posts should be searchable and filterable (so user can save category preferences) and listable (like index), and function like normal wp posts.
Maybe even a possibility for the advertisers themselves to be able to create the ad, view stats etc.?

I am SO open to suggestions/possible solutions and need to answer the client soon...

Thx in advance

/Claire