I have this off-and-on relationship with Quicken. Back in the day, when I barely had two nickels to rub together, I kept my Quicken data ruthlessly up-to-date, because my checking account would routinely dip below ten dollars. That kind of living on the edge calls for good record keeping. Once I got on my feet, and my financial situation was more stable, I lapsed into taking less care with my Quicken records. Then, when I moved from Windows to Mac, things took a turn for the worse. Quicken for Mac is, in a word, terrible. It's annoying to use, so that just made me use it less.
This weekend, I declared an official end to the Quickening. I switched over to using GnuCash, which really says something about the quality of Quicken if I'm willing to use an X Windows application on my Mac. Now, when I say "this weekend" I moved to GnuCash, I mean all weekend, and I'm still not done. Instead of typing out all the minutiae of double-entry accounting that I learned through trial and error (and error, and error) this weekend, just close your eyes and pretend that you're ignoring crushingly boring words that are actually here, as opposed to the ones you'll need to imagine.