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A few questions to ask yourself before buying into Yahoo:
1) How much traffic will you expect? I have paid for adult listings that are listed (alphabetically) quite high and got a few visitors a day. Make sure the section you are listed in is where you'll get the most traffic.
(You can test this by typing related searches and clicking on the Directory tab. The sections that come up first are obviously more likely to get traffic)
2) Google's algo used to be influenced by a Yahoo listing - if you were in for a related keyword you'd get a bonus (not sure about PR...). I don't know if this is still the case, you'd have to ask on the Google-obsessed SEO threads. If it does influence Google, it's likely worth the $299 (mainstream) listing ... likely.
3) If you are in the directory Yahoo has fun with search results. It often will list your home page and directory listing/description - even if the page that matches the keyword isn't the home page..
for example, Joe Viewer searches for "pink cotton candy" (I made that up). You have a page on your site targeted to (and called) "Pink Cotton Candy". If you are listed in the directory Yahoo may show your home page called "My Junk Food Site" where the words "pink cotton candy" never appear - the title or description. The result: Less click-throughs for Joe skimming through results.
I try to avoid the directory for reason #3 alone. Use their RSS feed tool to get your site indexed quick (and often) and if you build Yahoo-friendly pages then you'll get far more (targeted) traffic in their search results.
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