1. Always read the rules!
It's very important to understand if you qualify to enter a contest (by location, age, sex, demographic, etc.).  You don't want to waste time entering a contest that you cannot win.  You also need to be aware of  the start and end dates, the frequency of entry and how many entries may come from one household.  This is so important!  It can be once a day, week, month, once only, unlimited, bi-weekly and even odd variations on these.  The rules may state one entry per household or email address.  You may be able to enter your husband, wife and/or child, as well as yourself or you may only enter one person living at your address.  If you're not clear on this, you could easily disqualify yourself.  Read the rules!

2. Get a form filling program
This is important. Without an automatic form filler, you'll spend a lot more time filling out the contest forms. With a form filler, you simply click a button on your web browser toolbar and the forms are completed for you automatically. Google includes this feature on their free toolbar that you can download here. I use the Roboform program that you can get here. Both these programs add a tool bar to your web browser (Internet Explorer, Firefox, Mozilla or whatever). If you haven't done this yet, do it now!

3. Spam
I try as much as is possible, to keep the level of spam in my inbox down. When entering contests, some of the sites hosting these will use your information to spam you, so you must be careful to assess the site hosting the contest. Ask yourself if you trust the site that you are on. Be careful about what kind of information you give them, and what you agree to receive in return for entering contests. Read the entry form carefully, as there can be somewhat hidden check boxes that will sign you up for things you may not want. One way to avoid spam in your regular email address is to set up a special email just for contests using, gmail, yahoo or other free email hosting sites. The best thing to do when assessing a contest is to go with your gut. You will become more astute at recognizing spammy or scammy sites, the more you enter. Make sure you trust the company holding the contest.

4. Scams
Sometimes companies or people will misrepresent what they are doing, by enticing you to enter a contest.  You must go with your gut on this too.  Timeshare companies are notorious for doing this.  You enter your info into a ballot box somewhere and they call to say that you've "qualified" to win a big prize, and all you have to do is go somewhere and listen to a presentation.  Unless, you want to be sold a timeshare, say "no".  If the sponsor of a contest is unclear, it's likely a scam.  You should never be asked to pay for anything, in order to win a contest.  It seems that poetry contests are famous for scamming people.  I've heard of many who enter and always win (the prize is a book with your poem, but you have to buy the book!).  There may well be valid ones out there, but I wouldn't trust them.  Again, if you go with your gut, you can save yourself a lot of worry.  If you're told you've won a big sweepstakes that you don't recall ever entering, it just might be a scam.  You will never be asked for credit information or your banking information if you are a winner.  You should only be asked for contact information and possibly a skill testing question.  If you're sent a winning email, notice the email address of the sender--if it's unnecessarily complicated or doesn't add up to the info you have, then it's likely a scam.

5. Deciding what contests to enter.
The odds of winning a contest when there are a small amount of entries are much higher than when there are a large number of entries.  When prioritizing contests, I do make a point of entering local contests first, then regional, then provincial,  then national, then international.  If only certain groups of people can enter, this will increase your odds.  When entering international contests, you need to consider the tax and customs rules to receive the prize.  If the prize is worth it to you, then go ahead and enter, but sometimes people find it too costly to accept a prize from out of country.  If the prize is valued at more than $20 (last I heard), then you may have to pay customs and duty.  Couriers may add on extra charges.   You should check, if you win, what the charges will be and decide whether to accept or reject the prize.  This info is very general, and for more accurate answers about the charges for winning international prizes, check with your government's website.

6. Take a bit of time to look at a sponsors' website
Realize that these contests are intended to provide advertising for the hosting company, therefore, be sure to check out the site that they want you to look at, if you like it.  Sometimes, if I particularly like something I have been shown on a website after entering a contest, I will subscribe to a newsletter or order a product.

7. Organize your contests
I like to organize my contests, so that I don't inadvertently enter more often than allowed.  This way you make sure to enter using the correct frequency and get the maximum odds of winning.  I use my web browser's bookmarks to do this.  I have a contest file which has folders for frequency of entry.  Then I will go through the 'dailies' each day, 'weeklies' each week, and so on.  On the 'Properties' of a link, I will sometimes edit it to show the end date or any special instructions--this way the label will contain the pertinent info. 

8. Looking for Contests
I find contests by visiting sites that I like and looking for contests on them.  You can often find contests on magazine sites, television station sites, music sites, newspaper sites, store sites, book publisher sites, movie reviewing sites, tourism sites, city sites, product sponsor sites. So, think about your favourite mags, tv stations, kitchen products, and so on, and then go and search for them on the web. You may just find a great source of contest entries. When you find good ones, be sure to add them to your bookmarks and check them frequently. You'll get to know how often to review it. Good luck!

9. Thanks to the sponsors
This brings me to the appreciation for the sponsors of all these great contests.  Where appropriate, you should make every effort when you win a contest to thank the sponsor verbally or in a letter.  I think it's wonderful that all these businesses are willing to give away all those awesome prizes and think we should be encouraging them to continue, by making sure they know how much it is appreciated.

10. Best of luck entering contests!  Have fun winning!