:sunny: Actually you don't have to check the box everytime you enter. Just the first time. The only time I recheck it is on the weekly and monthly so I can see when I last entered. The dailys I enter everyday, so I don't recheck those and have the date that I actually started entering.
You do have to click the "Save my Sweepstakes" on every page that you have made checks. If you are adding them to your My Seepstakes you also need to click on the add at the bottom of the sweep entry.