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Could you answer that by tell me what has it done for you?
How long did it take to see a result?
If I go into the yahoo directory, will that help me get into DMOZ?
I am ranking number 2 and 3 for a very competitive search phrase in MSN, which I know is more dumb luck than anything else, I have been advised that I will need about another 200 inbound links from sites ranked PR4 or higher to get into the top 10 with google. I cant see a listing for my site in Yahoo at all for that key phrase, so I wonder if me paying the $299 will get me up there?
Namely - Having a link in the Yahoo directory helps to show the search engines (especially Google) what you should be considered an authority in (since humans edit the paid listings in Yahoo). Directory placement in Yahoo, generally speaking, is a good "vote" for your website.
A Yahoo directory listing alone is not the magic bullet to getting placed well in Google, but it contributes. If you are looking for a measureable ROI, I don't think you'll find the data at this point that will give you a thumbs up or down.
If you have enough money in your marketing budget to make long-term investments, this should probably be on your list.
My 2¢ worth is that your $299 would be much better spent hiring someone to find link exchange partners in your field (or just one-way links, which are much harder to come by). I had one of my sites listed in Yahoo's directory for one year and saw no tangible benefits. I suppose Google looks kindly on any site that a human editor has OK'ed (Yahoo, DMOZ, Joe Ant, etc.), but for me it certainly wasn't worth $299/year.
I'd go to rent-a-coder or elance and try to hire someone to find you good link partners. Over time, that will definitely help your rankings. Be sure to use good anchor text and vary that up a bit.
We all know what Google does when their algorithm is in jeapordy. They tweak the algorithm.
I say it here and now... and by no means is this a revolutionary thought:
The value of link swaps are going down and down. Google may, at some point, do a major tweak of their algorithm that results in a big drop in rankings for sites who rely solely on link swaps for link popularity (especially link swaps with sites that are not relevant to their content).
The best way to get quality in bound links is to develop good content. You can be proactive about how you use this content (you don't have to wait for people to find your website and link to it because they like it). You can leverage quality content in many different ways to get many sites to link to you for free. Just be creative.
Just be careful about the link swaps. It's true, they can be very valuable when done right. When they are not done right, it can be a complete mess. If you do get results, those results may not be long-lived. If you find someone who doesn't take a good approach to link swaps, you may find yourself linking to websites that are not related to your own, which can create a very serious problem (Google judges you by who you link to, and if you link to bad sites, it hurts the credibility of your site).
I can't tell you how many times clients come to us after working with "seo" firms who setup these massive linking campaigns that are in clear violation of the very SEO principles Google lays out on their site (all about google > webmasters).
Ideas related to my post about leveraging content:
Offer your valuable content up to other websites who target the same people you target (non competitors though). Allow them to post an article you've written in exchange for linking back to you. If the article is good, you can many relevant links (in-bound, high quality, very relevant).
This is actually a service we provide, but if you are willing to put the time in, you can do it yourself - and you'll find a 0-cost way of generating 1-way links.