Does the domain name extension matter?

As far as search engine listings go the extension does not matter.  There is no difference between .com and .info domains as far a the search engines see it.  However, if you have a country specific extension like .jp or .uk then it will have effect on your search engine listings because you will just be listed in the country specific engines like Yahoo! Japan.

The other issue is whether or not you will lose credibility with your visitors if they land on a .info versus a .com domain.  For 95% of the visitors out there I don't think they know or will notice the difference in the extension.  Nor do I think it will effect their purchasing plans if your website looks professional.  If you are worried about this issue then you can have your money sites (where you redirect your visitors) be .com domains and your cloaked sites be .info domains.