Affiliate Marketing Secrets

Here’s what I’m after:
An out-of-the-box web application that would allow me to create a set of questions that points a potential buyer to the product(s) they’re looking for?
If there isn’t such a beast, I’d also be into the following:
An application that displays a table which can be sorted and filtered on-the-fly to the users’ preferences.
Here’s my scope:
I have a website for niche enthusiasts, and I want to help my visitors, who are new to the niche, find products that are best suited for them (trying to make an interactive first-time gun buyers guide). The list of products is roughly 200, and will easily grow to 500, spanning over 20 different product feature characteristics (currently 20 columns in an Excel spreadsheet).
If there’s something out-of-the-box that meets what I’m after, I’d be happy to pay for it, but free is always nice. I have very limited programming experience, but if there’s an open source application that I could tweak, I’d be willing to grab a book, and figure it out.
Note: If you have an application in mind, but it’s a plugin/extension exclusive to a specific CMS, please let me know. I’m currently building the site on WordPress, but I’m flexible if it fits what I’m after.
Sorry ahead of time for the broad, abstract question; it’s one of those things I don’t quite know how to Google (I mean Yahoo) for. Thanks in advance.

I already know this is not an easy task and I would drop the idea altogether, but I really love my dating site niche idea. The reason I want to start it is because I myself went looking for this particular niche and could not find anything out there. Even the few sites I found that somewhat serviced my niche were poorly made and had bad layouts; however, even they got members because there is nothing out there.
As for dating software, the prices are ridiculous! How is someone supposed to make any money at all without going broke first with these programs? I’m not saying I wouldn’t pay a one time, couple hundred dollar fee, but close to a thousand plus monthly payments over 40-50 dollars is crazy.
Despite knowing my way around creating websites, I have no programming experience to create something like this. I have looked at osDate but it seems most of the sites that use this script fall out. If someone can point me in a direction or at least give me options, I would be very grateful.