My mom says I’ve always been lucky. She says that because I’ve won a lot of things.
The earliest prize I remember winning is a Star Wars patch from Dixie Cups. The grand prize was Darth Vader would come to your party. The entry form was on specially marked boxes. I recall they gave away 1,000 of the patches. That was back around 1981 or so.
Years later, I was working at Walt Disney World, and I entered in a drawing at the local grocery store for a turkey for either Thanksgiving or Christmas, and I won.
In around 1995 or so, I subscribed to a sweepstakes newsletter for a year or two. It came in the actual mail and provided all the information to mail in entries in hundreds of sweepstakes. I entered everything that had a prize I was remotely interested in, and I won about one prize a month, mostly small items. I still have a contact lens case that I won; I never wore contacts, but I keep a few headache pills in one side and allergy pills in the other. One of the larger prizes that I won then was an autographed hockey card; I forget the guy’s name, but he was a fairly major player at the time, and I sold it for about $75.
For several years in the 2000s, I subscribed to an online sweepstakes clearinghouse. It was like the newsletter times a thousand, plus there was a forum where all us sweepers shared answers for contests* and shared our wins. During that time, I entered sweepstakes voraciously online. I spent several hours a day typing my name, address, and phone number. When you enter that volume of sweepstakes, your name is bound to get picked once in a while. That’s when I got really lucky. I won $10,000 cash in one, $5,000 cash in another. I won trips to New York and Los Angeles. Bunches of small prizes – DVDs, books, coupons for free candy and soda. Sometimes I’d get notification by email that I won. Other times prizes just showed up in the mail. It was really exciting and fun.
When the recession hit, and as blogging took off, sweepstakes started changing. Companies learned they could get a lot of mileage out of having bloggers write an article or product review, and they’d provide a few samples the bloggers could give away through their site. Ten or Twenty bloggers might be offering the same prize. I won some cool items like that – one of the best was my first DNA test from 23andMe – but it didn’t seem like many companies were giving away the big checks or cars or vacations, not like they were.
Then I injured my wrist. I was taking out a bag of dirty cat litter, and somehow my wrist twisted oddly, and I kept thinking it would just get better, but it didn’t. As I tried to help it heal, I spent less time on the computer at home (since I had to type all day for work). Finally I saw a doctor and had surgery, and then it took a while for it to completely heal, and in all that time, I got out of the habit of entering sweepstakes.
Now, of course, I spent all my computer time doing genealogy.
*Contests vs. Sweepstakes: A sweepstakes determines winners by random drawing. Contests require you to answer questions, complete a task, or submit an entry to be judged. Some hybrid-style giveaways require you to submit a picture, but the photo itself isn’t judged; they just pick a winner at random.
Rhyme Schemes and Daydreams 
Goodness! That sounds like a lot of work, but at least you got a payoff. I recently went to a real estate open house and won a bottle of wine. That was nice.
It’s always a pleasant surprise to win! The key is to enter whenever you can, and beware of anything that seems spammy. I used to work in a mall where the hot tub store always had a drop box out. Nothing on the box or the entry forms specified the dates for entry, when the drawing would be held, or when a prize would be awarded. Nope!