There are thousands of sweepstakes and contests online. Most are legitimate and are run by reputable companies but others can be shady and are simply a way of gathering email addresses. The trick is to find the good ones and this is where I can help. I do my best to find the most interesting contests and sweepstakes and list them here on my web site. My work will save you hours.
Find any sweepstakes to enter. It's not too hard to find sweepstakes. You can enter them at the grocery store, at the bank, at fundraisers, or on the internet. You might even get invitations to enter sweepstakes in the mail! You probably want to enter most of these sweepstakes of course, but if you're really serious about winning, you need to actively seek out sweepstakes.
Speaking of overnight delivery: it's just not worth it. Like entering sweepstakes that require a purchase, paying exorbitant postage is a waste of money–money that could be spent buying stamps for a lot of other sweepstakes. If you're entering a contest (a competition based on skill rather than luck), you may decide that special delivery is worthwhile if you've got a great entry.