$4000 in Hole! How can I Recoup Membership Site?

Hi: I bought the Membergate software about a year ago. I have a website that offers legitimate work at home jobs. I researched every single job myself from my 10 years of working from home I learned how to weed out the scams and thought other people would appreciate a site like this. I charged $9.95 month with a $1 - 7 day trial. Well after 1 year I only had a handfull of people who stayed past the 7 day trial. I basically lost $4000. So now I converted it to a Free membership site with the focus of making money via affiliate program links on some jobs, and later plan to add ebooks, ad space, etc. I converted it 45 days ago and have since had a whooping 295 members sign up! Impressive but I'm not making a dime!

Can someone share with me how I can possibly make this site profitable?

I thought about those sites where in order to sign up/register you have to register for at least X amount of sites. This way they can sign up for a few affiliate sites from the beginning and at least I can make a couple of bucks for all my hard work. It would not be any annoying sites that make you buy anything etc., just other free job sites.

So how would I go about making this part of my registration process? Does this sound like a good idea? What type of coder would I need hire to implement this into the registration form and does anyone here d this type of work?