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Any software recommendations?
Needs to be easy to use.
Price needs to be under $2,000
1st - there are several directory software programs that let you make "yahoo style" directories and all of it can be managed online. There is one in particular that I think it $299.
secondly there are several open source CMS (content management system) of varying quality, all of them either free or cheap here is the dmoz category [directory.google.com].