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I have found that Looksmart, Inktomi, DMOZ and Yahoo's directory have really helped my listings. All of these are paid except DMOZ. You can also another important engine to get into is Google, to get a better idea of what Google is looking for go to the home page. Brett did a great post as to what Google is looking for, I dont have that post off of the top of my head. Hope this helps.
Not at all. Inktomi results are presented after all the Looksmart results, so even if you have a number one ranking in Inktomi, it still will not go near as far as a listing in Looksmart. The traffic from MSN alone is well worth the Looksmart investment.