First, is the site related to yours and are the visitors to that site your target audience? Would Google consider it a natural fit?
Second, Is the site willing to offer up traffic reports to help you do a cost analysis? If you spend $25.00 a month for 25 clicks, this is not going to be worth your while. Ideally you want each click to cost as low as possible as not every click to your site will convert. Look at your own sell through stats via EPN to get a good idea of how much a click through to eBay is worth.
Third, is the site you are wanting to advertise on a captured audience like a forum or a heavily commented on blog? This type of traffic is golden and can be engaged quite easily if your own site has great content.
Fourth, will the owner consider a month by month deal so as you are not locked into a bad deal?
Fifth, is the site blatantly selling these ads? If so, will he ensure your link has the nofollow tag as to not get you in trouble with attempting to buy page rank?
Buying links on related sites is a risky business deal regardless. I have some purchased ads do fantastic and are well worth the price, while others where just dogs. Knowing your own EPN stats and tracking the incoming purchased traffic will let you know in a hurry if it is indeed a lucrative deal. You could also just consider buying a site review in the form of a blog post or forum post to get a feel for that sites converting power, before leaping into a bigger commitment. Start small budget wise before moving up. Always and I can not express enough, always make sure the site or page you will be buying traffic on is related in some sorts and always ask for a nofollow tag if you are unsure if the site is a known link seller or a bad neighborhood.
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