I didn't realize I had so many tips for entering contests stored inside this crowded head of mine. I have learned so much over the years and I love sharing them with you! Another tip that hit me in the middle of the night is that you should enter contests that offer more than one prize. This gives you a greater chance of winning something, even if it isn't the grand prize offered. When you get that winning notification, you'll be encouraged to go out there and enter more contests!
Contests that have shorter entry periods give you a better chance of winning than those that last for a year. The longer contests last, broadens the chance of more people finding it and entering it which lowers your chances. Those contests with shorter entry periods give you a greater chance of winning because many people are not on top of the contest game.
Another interesting tip would be to enter those contests that have restricted states. When looking at rules, I notice that Rhode Island hardly ever gets a chance at entering contests. I don't know what their problem is, but I feel so sorry for those people who live there. Florida and New York are also excluded from a lot of contests. One day I'm going to either research this or figure out why all by myself (and then write a book – you remember that book tour I was dreaming about a few days ago …). Alaska and Hawaii are omitted at times mostly because it cost more to ship to those winners. Just make sure your state is listed in the rules, or you will be wasting time entering these restricted contests.