How would I set up a site that would show members ads based upon the interests they set up in their

I want to create a website that is a membership site. It will have 2 account types - Advertisers and Members. I want to allow advertisers to place a certain number of ads per month for a to be determined fee. I want to have members fill out a form when signing up as members where they select what their interests are. I then want to be able link members to ads that relate to their interests.

Also, I want to set up auto notifications to members that are based on their interests and the frequency they set for notifications to be sent to them. I also want to make the site searchable by parameters such as cost, date, type of event, etc. Ads need to be able to be RSVP'd to and allow payment online if the member wants to pay for the event online. Also, I need to allow members to access their profile, billing, etc. I want to also allow Advertising members to pay for additional ads on a per ad basis once they have exceeded the monthly limit.

I know I can use the Membership plugin to create the membership site but am looking for ideas on how to accomplish the other functionality.

Can anyone tell me how to do this?