Seeking plugin or combination to achieve specific ad serving goals

Hey all and thanks in advance for any assistance. This is day 1 using WordPress and I’m having a great time reading all these threads and seeing how easy WP is to leap right into!

I wanted to post this before I got too deep into customization for fear I might somehow limit myself to options of what I believe may be a plugin or combination thereof. Hopefully someone can make some recommendations because I am daunted by all the options, and fearful at the endless investment of time I could spend if I tried out each one!

In a nutshell, I need a membership database and a advertisement management system. I want the member database to have survey/interest recording, which will tie into the ad system. So if you aren’t a member/logged in and were on the Cars section of the website, you would only see Car ads; however if you were a member and had selected you liked Toyota and Lexus then you would only be served Toyota and Lexus ads when in the car section. The same would follow for “Shoes” ie: general shoe ads or branded breakdown for “Nike” and “Reebok” for a member.

So basically the ad system needs to recognize my websites categories as well as query my membership database information.

Any recommendations are so greatly appreciated!

-Colin