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Do I have to keep entering contact info time after time?

No.  Some contacts, such as lawyers and lenders, are associated with more than one file.  One of the features of  Hotdocs™  is that you can define a "pick list" of a class of information, such a lawyers, which can be updated automatically while you enter the information on a file.  Once a lawyer is added, the information will be there for the next file on which she is involved.  The list just gets bigger and more valuable the more you use the templates.