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What is the current opinion of paying $299 for the Yahoo Directory? p.s. I have 300 Websites. They are each city based so I would be way down in the Regional-->USA-->State--->City--->City Directory
I predicate this with saying that I haven't dealt with Yahoo.com for a while, as I target yahoo.com.au, but as your sites are geographic, I'd be inclined to try for free standard submission for 2 or 3 of the important sites first, under the appropriate geographic categories, especially if you have good content.
Do the usual wait and see (email usually within 3 weeks if accepted) for which, if any, gets in for free, monitor the referring stats and then decide whether it's worth your while to continue free submissions, or it's cheaper for you time and money wise to pay to be sure they get in.
Personally, as Yahoo has deprecated the directory so much (almost "below the eyeline" in 1024x768) in favour of the search (for now), I prefer the free submission for now.
It takes a bit more time, but you get to know the directory and structure, find stuff (like competitors you didn't know you had! <grin>) and when the time comes that Yahoo decides to improve the directory profile or factor SERPs from the directory again, you'll already be there!
Hope this helps, good luck.
Cheers and Hooroo