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>Will I see any increase in hits by paying the 300 bucks for inclusion?
Not necessarily, do a few searches at Y! for the keywords you'd like to rank well in and see what kind of results come up. It's very important to get some of those keywords in the description and title of your Y! listing (of course the Yahoo editor who adds your site has a lot to do with that) so be sure to write a well crafted title and description using the examples from your searches as a guide.
Very few people drill down through the directory structure at Y!, so if your site doesn't come up in searches your listing is largely wasted, many go for a Y! listing for the boost they get at google, but it sounds like you don't need it.