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When I first submitted to Yahoo 2 years ago, I treated this $299 investment as a guranteed PR transfered from an authoritive site. Both Yahoo and Google gave credits to having a Yahoo listing in their SERP. Now it seems like this is not the case anymore. As far as I can tell, google gives less and less importance for directory listings from DMOZ and Yahoo. This $299 you spend for a new listing, you pretty much get nothing in return except for a buried-deep listing that nobody ever sees (unless your site is already VERY popular to begin with).
I will for sure keep my current listing, since it is already quite popular and there is still hope that it will crawl back on the first page of the yahoo category. However, for new listings, it really makes me wonder if it is really worth it to have new sites submitted to Yahoo.