directory plugin import and using membership plugin

Hi, I would like to purchase the directory plugin, however a couple of questions. First question is I have a directory of 2000 or so listing which would have to be moved over, would this be a difficult process through cvs? Second question, if a customer chooses the membership option then lists their business, is there a way to prevent them from being asked about membership again? Right now, people can choose a membership option when creating a login or when they list a business, without the current directory being integrated with the membership plugin.