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Is it sill worth getting that 300$ directory listing? Would there be any noticeable benefit?
I'd hold your money for a month or so to see if Yahoo starts using Ink and how they will use it.
You'll here all sorts of ideas about whether or not it's worth it - in reality, it'll depend.
For the PR value - don't bother. If you think you can get traffic to the site, then it's worth it.
That's my opinion.
As time permits I'm wading through some research papers I ran across that touch on the value of being listed in authoritative directories. I don't know if the concepts are still valid, but as 2_much suggests, depending on what Yahoo does with Ink we might try Express submit for a site.
People type the keyword and click on the categories that are returned on top. These sites happen to be listed towards the top of the list (alphabetically) so they get a lot of traffic.
So sometimes it's worth it.