is there such a thing? or is the cheapest the $299 one.

There is such a thing for most categories. Submit a site.

Worthless, in my opinion right now, though.

Yahoo uses Google right now so just submit to Google.

True, Yahoo uses Google to display most search results.

For free listing on Yahoo, as long your submit in a non-profit or non-business related categeries, it would be free. Else gotta pay 299 for the listing, which is expensive.