I've always noticed that when I consistently weigh myself on a daily basis, I more easily maintain my weight and can more rapidly achieve my weight loss goals. According to two recent studies (the first by the University of Minnesota of 3,000 overweight men and women and the second by Cornell University), researchers determined those who weighed themselves frequently had greater weight loss than those who did not.
I feel that this strategy works because people gain (and lose) weight slowly; For this reason, you could put on a pound every couple of weeks and not really notice a change in your body composition until you have gained 5, 10, or 15 lbs. Because weight is gained slowly, I think that weighing yourself daily gives you the chance to steer your weight on a more consistent (daily) basis, after all, it's easier to lose one pound (after you have realized that you have gained it) than it is to lose fifteen.
I always try to weigh at the same time everyday - in the morning before I eat breakfast or drink anything. This allows me to get a consistent dry weigh-in and track my progress more accurately.