The more difficult a sweepstakes is to enter, the fewer qualified entries they will receive. If you have to answer a difficult question correctly, or if you have to spam a hundred of your closest friends, you'll have better odds. Difficult sweepstakes are pure gold, but be sure to separate difficult from unrealistic (that is, you have to spam 100 of your closest friends and they all have to enter their email addresses on a website).
Choose which sweepstakes to enter. Not all sweepstakes are created equal. For one thing, if you have to buy something to have a chance to win, don't enter. If you have to complete some sort of program (which usually entails buying things) to enter—–those annoying pop-ups for free iPods come to mind—–don't enter (unless it's realistic to complete and free); remember that a lot of these opportunities are about gathering personal information to bug you with advertising down the track. There are plenty of chances to win without jumping through hoops or wasting your money. Beyond that, your decision to enter should be based on your own preferences. Here are a few things to consider.