I’m pretty good about registering shareware. If I try a program and really like it, then I register it; operating system ease of use aside, indie developers are why I love the Mac. Out of the seven or eight programs that I always have running, only two are Apple software (Mail and iTunes). The rest are shareware (including such gems as LaunchBar, PathFinder, NewsFire, DeskShade, and MenuCalendarClock iCal).
However, I only recently registered MenuCalendarClock. I was only using the free features, and iCal integration wasn’t worth $20 for me. It was recently on sale at the MacUpdate Promo, though, so I picked it up as a thank-you to the developers (assuming they get any money from those deals at all). Before I registered it, though, I turned on some registered-only features to see how long I’d been running it unregistered:
908 days. 908 days. I think that’s some sort of personal record for me. The only rival is the amount of time I had Bubble Trouble unregistered back in the 90’s, but I think I still kept that under a year.