Where the best chances are

Local contests are easier to win because fewer people can enter. Countless bloggers are offering prizes, too -- what better way to get readers? -- and some of these giveaways have few to zero entries. But even with a well-known blogger your chances are pretty good, because you need to be one in a thousand, not one in a million.

Follow your particular focus. For example, parents should check out mommy blogs for the chance to score everything from board books to eco-friendly disposable diapers. Or even school uniforms: French Toast regularly stakes bloggers with polos and pants to give away, and recently ran a contest with a $10,000 cash prize to one family plus $5,000 worth of uniforms for a local school.

Such specifically targeted contests mean reaching fewer consumers -- but the right ones. A child-free reader isn't interested in school uniforms, and a Luddite wouldn't want a laptop.

Savvy sweepers share secrets

Noah Fleming's winning streak was made even more valuable by the fact that Canada (unlike the U.S.) doesn't require citizens to pay taxes on sweepstakes winnings.

Over the past couple of years the Internet entrepreneur has won, among many other things: an all-expenses-paid trip to the Montreaux Jazz Festival in Switzerland, two Xbox 360s and a number of games, concert tickets, a 20-inch iMac, an autographed hockey jersey, an iPod, a Tassimo coffeemaker, a 46-inch television, a home theater system, DVD boxed sets, a Wii, a Flip Mino HD camera and two Dell laptops.

"Luck" had nothing to do with it, Fleming wrote in this post on his website. It was simple persistence -- "and you can do the exact same thing."

A few more (sometimes conflicting) tips from the pros:

  • Enter everything. Not having to "analyze every contest" means you can enter more of them, according to Troutt. You can always turn down a prize if you don't want it, she says. But there's another school of thought, which is . . .
  • Be selective. Would you really ride that mountain bike or use that golf weekend? If not, then let someone else win. And there's another approach on this, too . . .
  • Sell things you don't want/can't use. Some sweepers are horrified at the idea. Others suggest that the money you make could offset taxes, get you through lean times or help you build a stake.
  • Check out Twitter. Sign on and search for the word "win." You'll get a bonanza. Or search by end date, e.g., "ends 12/10."
  • Consider a newsletter or website. Some charge but may offer a free trial. Others, like SweepsGoat and Prizey, are free. Online-Sweepstakes.com has both free and premium sections.
  • Multitask. Sweepstakes are relatively simple to enter, especially if you use software that fills in contact information. "I would die without Roboform," says Troutt, who enters at least 400 contests during each 10-hour overnight shift as a hotel reservations agent. (She works at home and uses a separate computer during quiet spells.) Click that Roboform while you're watching TV, or waiting for a friend to show up at the burger joint. Or, like Fleming, while you have your morning coffee.
  • Prizes = presents. Remote-control cars, MP3 players and other items go well under the tree or at the many birthday parties your kids attend. The fisherman next door might appreciate the foam cooler. "There's nothing like walking up to somebody and just handing (something) to them," says Carol McLaughlin, who publishes This n' That Sweepstakes Stuff. Or you could . . .
  • Donate your winnings. Toys for Tots always needs gifts. Family shelters and senior centers could make use of toiletries, robes and other small items. That spa gift basket would make a swell door prize at the next PTA meeting.
  • Set a Google alert. Troutt uses "second-chance drawing," because these have decent odds.

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  • Bookmark local TV/radio sites. Troutt checks these once a week. In the past five years she's won 10 trips, theme park and concert tickets, jewelry and other items.
  • Follow your faves. If you love Coca Cola or American Girl dolls, "like" their sites and watch for giveaways. Remember to follow local sites, too; twice in recent weeks I have won free meals at Harley's Old Thyme Café in Anchorage, Alaska -- just in time for my Christmas vacation. Sweep on!
  • Don't forget about taxes. If you're lucky at contests, you'll need to claim the value of your winnings at tax time. If you're not sure how a big-ticket item will affect your filing, you should consult a tax professional, call the IRS at 800-829-1040 or visit the IRS "Help with tax questions" page. Contest sponsors usually send a 1099 for items worth $600 or more.

Donna Freedman is a freelance writer in Seattle. You can find more of her writing on MSN Money's Frugal Cool blog and at Surviving and Thriving (motto: "Life is short. But it's also wide.").