Most of my success with sweepstakes wins has come from entering daily sweepstakes, whether they were instants or just regular sweeps. If the sweepstake runs for a long period of time and I enter every day, or nearly so, then my odds seem to be pretty good. It seems like most people give up after just a few entries. That's one reason why I make a point to hit the big daily sweepstakes every day.
Some sweepstakes have prizes that don't absolutely thrill me, but that I'd still like to win. It might not be worth the effort to enter every day for months, but the win would still be nice to have. These are the kinds of one-entry sweepstakes that I like. I try to get a single entry in before the sweepstake ends, and then I don't have to worry about it anymore. My chances won't be better than any other entrant, but then again they won't be any worse.
Creative contests I usually enter when the task seems simple, like a short essay or a recipe where something springs immediately to mind. Sometimes the wins really surprise me. For example, I've never thought of myself as a greeting card writer, but I did win a nice prize for coming up with a saying for a Christmas card. That was one of my most fun and exciting wins, because it wasn't a reflection on my luck or dedication, but also my writing skills.
What about you? What kinds of sweepstakes do you enjoy entering the most? Fill out the poll and let us know!