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.

There are thousands of sweepstakes and contests online. Most are legitimate and are run by reputable companies but others can be shady and are simply a way of gathering email addresses. The trick is to find the good ones and this is where I can help. I do my best to find the most interesting contests and sweepstakes and list them here on my web site. My work will save you hours.
Georg and Laurenz Theisinger was the only father and son team to fly during the 15m German Championship in Marpingen. The team flew very well with Laurenz winning Day 7 and Georg, after their out landings on Day1, managed to still finish strong in third place overall. Georg shares more about their adventure. JS had the privilege of exhibiting at the recent Austrian Gliding Day, well organised by the members of the Austrian Gliding association.  Uys Jonker had the opportunity to tell how a new product is born and spoke about JS’s exciting new products. Pilots also had to opportunity to test fly the JS3 the next day in Mariazell...
Know your odds of winning. You usually don't know what the exact odds of winning are because it will depend on the number of entries. You can, however, estimate the odds. If you get an entry form in the mail for a sweepstakes with a huge prize, you can be assured of a ridiculous number of entries. If you see a jar at a local restaurant for a free lunch, however, you know your odds of winning will be much greater––you may even be able to see how many entries are in the jar.
The Golf Pick'em Challenge Contest challenges your visitors to successfully select the top placing golfers of each major tournament and win up to $1,000,000. Contestants also have access to schedules, standings, interesting stats, polls, and the "Buddy Tracker" (this is a feature that allows contestants to track the scores of friends playing the contest, along with their scores, to see how they stack up against one another). more» 

Space out your entries. Assuming that the number of times you can enter is constrained, either by the rules or by your budget, don't send in or drop in all your entries at one time. Wait a few days or weeks (depending on the contest) between entries so that when the entries get mixed together you've got a better chance of one of your entries landing on top.