Winning a Contest can sometimes be a challenge. Even the Well Seasoned Serious Sweepers go through Dry spells.
But the More you enter the better the odds.
Maximizing each contest will improve your odds. If the contest allows Daily Entries ~ Then try hard to enter the contest every day. If your only entering daily contests weekly ~ your odds go way down.
Be Consistant ~ Get into the Groove of Entering your contests in the evening while watching tv, or when the kids go to bed. But pick a time, so you can start getting into a routine of entering contests.
Some Contesters say it takes up to 700 contests entered before you win! I’ve also heard it takes 3 months, to start winning. Some people win right away, and others need to wait it out.
Wins Generally Start out rather small.
A Few years ago ~ I got all set up and started entering contests, I actually won quite a bit in a short period of time. I won $100 Gift Card to HMV, 5 dvd in a package, and then a palm pilot. This is about 5 weeks into it. I didn’t even get emailed I had won, some of the stuff just “showed up” The only thing I was emailed on was the palm pilot and I had to send back a prize claim.
If your like me and Very short on time. You can always simply enter the contests that state ” One entry per person” as your odds are the same as anyone else of entering.
You must be Patient. It will not happen over night.
Another good Odds one is Twitter Party Contests. As it’s timed and many people can’t make it, or find twitter difficult to navigate and give up too easily.

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Not too much of a contester myself. Only when it is something I really want. However very happy that my daughter is. We both just won a $100.00 gift card from Cogeco today. Yippy -she nominated me as an everyday hero and now by winning “she is my HERO” lol
Its like you said sometimes you win right away and sometimes you wait for months.