As the names imply, Daily Entry Sweepstakes let you play once each day and Single Entry Sweepstakes only let you enter once over the entire sweepstakes.
Daily Entry Sweepstakes
Advantages: If you get started early and are diligent to play every day, you can have a significant edge over many of the other players. For example, if the sweepstakes runs 30 days and you play every single day, you will end up with 30 entries. Someone else might be lazy and only play it once, or find out about it late and only get a few entries in. Now you have a way better chance of winning than those people.
Disadvantages: If you find a daily entry sweepstakes late, or you don't have the time to be entering every day, you will have a much lower chance of winning.
Hint: Win.ly's Tracking and Liking features let you easily keep track of the daily entry sweepstakes that you want to concentrate on. Make sure you are logged in and then "Like" the daily sweepstakes you want to play every day. Then when you return to Win.ly each day, just click on the "All my likes" link in the My Likes section of the home page. (Or if you are on Win.ly Premium, just select "Only my likes" from the Likes pull down filter at the top.) You'll see the sweepstakes you are tracking along with the last time you visited. This is a handy reminder to help you play each day. It also tracks how many times you've visited as a reminder to how many entries you are piling up.
Single Entry Sweepstakes
Advantages: The advantages of single entry are the exact opposite of daily entry. You can find a sweepstakes you are interested in on the very last day and still have as good a chance of winning as anyone else.
Disadvantages The disadvantage is that even if you find one early, there's no protection against late comers. Where as with a single entry you can start amassing entries, here you just get your one. There's nothing to protect you against a big wave of entrants on the last few days that water down your chances to win.
Furthermore, it is rare but not entirely uncommon that a game will let you fill out the registration over and over even though you only ever get one entry. This is another reason that seeing the "Single Entry" designation on the Win.ly screen is helpful, it can save you from lots of wasted time on sweepstakes like these.
Different Strategies for Different Games
So hopefully you see how knowing these little strategies can help you win more. Of course the best way is to know which games have the best odds with Win.ly Premium, but these other strategies also help a lot.
Good luck and keep clicking those "I won" buttons!
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