What if you end up on the 14th page on the Web Site Hosting category? How worthy of a link can that be?

Another bit is that you pay the $300 but there's no guarantee your site will be listed. You also have to pay $300 per year to maintain your listing there.

I would say there are safer and more targetted places to spend $300, and they should the focus of your search, especially if that's a relatively big chunck of your advertising budget.