Do I charge my customer for the service, do I charge the dealer or make it free for them and charge for advertising on the site?

Darren. 

This is a common dilema. 

As I understand your primary issue;  you have no paying custmers, you have non paying dealers,  and you have advertisers.

The first thing I would do is create value.  Charge the advertisers a fee -if they are most approachable. Or do everything for a free-trial period. Take credit cards. then, after the trial period (30 days) charge everyone the appropriate amount for using your site.  After 30 days they either love it or leave it. So, essentually you have 30 days to create value.

Darren I agree with David, in addition I would consider the fact that 39.99 is kind of a big hit, its easier to offer a free purchase, let them know the savings and let them pay a small fee per month, like a subscription to access your deals. Its hard to sell something when no one knows what it is so i would say let them taste it before you charge them,

My website is www.find3bids.com and I help people get the best price possible for the piece of construction equipment they are looking to buy, by shopping it around at qualified area dealers. I can't charge a monthly subscription because no one buys this type of equipment frequently. If someone is going to buy a $70,000 manlift, why wouldn't they pay $39.95 to save thousands of dollars on that purchase? I guarantee they will save 10 times that much on the purchase price or I refund the $39.95. And I do all the work contacting the dealers. They remain anonomous to the dealers, so they don't have to worry about 10 salesmen calling them all the time asking them about the deal. I see value in my service, but I guess I am the only one. Let me give you an example:

A home builder in South Jersey was looking for a JLG Towbehind lift. He had a price and delivery date from a qualified dealer. I sent it out for bid and got him a lower price by $3200.00 and a faster delivery date. Now why isn't that worth $39.95?

Darren.

To follow up on your last post- thankyou for the additional info. this gives us a better perspective of your site. 

I'm thinking (maybe I'm wrong) that your site is "somewhat-similar" to an auction site. Therefore, perhaps you can charge a commission on the winning bid.

Per your example:   A home builder in South Jersey was looking for a JLG Towbehind lift. He had a price and delivery date from a qualified dealer. I sent it out for bid and got him a lower price by $3200.00 and a faster delivery date. Now, charge them a commission of $39.95 (if that is an acceptable margin for you).  Using this approach, as Robert said , "Its hard to sell something when no one knows what it is so i would say let them taste it before you charge them."

Darren,

Everyone answered this well and listen well.  My experience with websites, like yours, is that business owners have a great product or service and want to start with a website.  I would venture to think that you have a list of vendors and customers.  Since you are essentially a middle man, your address book is your most valuable asset.  Use your voice, call people, let them know it is available as a convenience for them.

Some other points:

1. What is your vision?  Who are you serving, primarily - customers or vendors?

2. Do  you want the site to make additional income or a single source of income?

3. Rethink the website and its purpose - it may have a stronger value as a supporting tool.

Peace,

Chris

www.TheChrisGroup.com