This conversation got quite derailed and I didn't see any helpful answers that I could follow. Can someone jump in to answer the 1st question clearly?

How do you take the files from QB2008 and transfer them to an updated version of QB, as f-s-vanmastrigt asked in the original question. 

We did not update QB a few years ago because a salesperson at Intuit told me it could not be done. I don't believe that. I'd like my categories and all my data to transfer clean.

Help! Thanks.