I started using Quickbooks in 2001. Prior to that I had been using my own system, written in Perl with an HTML front end. I don't remember now what convinced me to switch away from that, but honestly I wish now that I had just stayed with it.
I originally used the Windows version of Quickbooks, but switched to Mac a few years ago. That was a mistake in some respects: the Mac version lacks many, many features that are found in the Windows product. However, I was tired of maintaining a Windows environment simply for one program, so I switched and have simply suffered the missing features. It's not all that horrible - if you didn't know the Windows version had the features, you wouldn't even notice most of them. It's mostly that I was accustomed to certain shortcuts and so on that disappeared when I switched.
The BIG problem I have had with Quickbooks has been data corruption. This existed before switching and after switching, so I can't blame the Mac version for that. Nor am I alone in this problem: there are several companies that offer Quickbboks data repair services.
I suspect most of this comes from Quickbooks never having a "close out year" or "rollover year" function. There is no year end procedure in Quickbooks, no rollover, no closing of a year. You just keep on trucking, and your data file grows and grows..
Well, somewhere between 2001 and when I first realized I had problems, they did add two somewhat related functions. One is "Verify Data" and the other is "Condense Data". Unfortunately, by the time I noticed these, my data file was alread out of whack and those just crashed and burned.
The corruption manifests in little details: a customer who shows up in A/R reports with a balance, but there are no unpaid invoices and no balance to apply an adjustment credit to. I have similar oddities in sales tax calculations. It's all just a mess.
I could contract with one of those Quickbooks data repair firms, but I decided instead just to start over: start a new company file for 2011 and go forward from there, verifying and condensing appropriately in years to come.
On the face of it, this seemed like a reasonable thing to do. Quickbooks has an export function that will kick out some data to files that can even be loaded into a spreadsheet. I exported customer lists, vendor lists, my chart of accounts and my sales item lists that way and imported them into a new company. We then went in and added in all outstanding invoices and accounts payable, plus a starting bank balance. That part was easy enough, especially so because December has been slow and there were less than a dozen outstanding invoices to re-enter.
Quickbooks for Windows could have transferred my custom invoice formats, but for the Mac version, we had to design them all from scratch. That was probably the most annoying and time consuming part of the work.
If I had just a little bit more energy and time to spare, I would take this "starting fresh" opportunity and go back to my own custom written bookkeeping. I may do that yet: I'm really not happy with Quickbooks and could get exactly what I want by writing it myself.