Sweepstakes is a great hobby because you can spend a little time on it or a lot. And unless you're very lucky, you'll only see a few wins if you spend a little time on it. It's like the old saying "The harder I work, the more successful I am". The more I enter, the more I win.
That said, here's a few basics to get you started:
I highly recommend an e-mail address seperate from your personal one. I can't recommend gmail enough. I'll talk in a few days about blog giveaways, and you need a google ID for many of these, so I would say gmail is the way to go.
The next thing is always be sure and follow the rules. If it says one entry, don't try for multiple entries. There's more sweepstakes out there than any one person could ever enter, so if it's a one entry, just make your entry and move on to the next. Other things to watch for is eligibility. Some might only be open to certain ages, certain states, etc.
Be ethical. Don't enter your dog just because he has a name that sounds like a person. Or if you're in a voting contest, don't devise ways to cheat the system and get more votes than you are allowed per person.
A few things you need:
To do online sweepstakes, you need a computer. I highly recommend the site http://www.online-sweepstakes.com/ because they list so many sweepstakes, (as of tonight there are almost 8,000 different giveaways listed on this site.) I do recommend upgrading to premium if you enjoy it because the most "winnable" sweepstakes are only able to be seen by paying members. I also recommend the program "Roboform" (there's a free version of it that does NOT store passwords). It makes filling forms so much easier. Really a computer, and Online Sweepstakes is all you need to get started to enter online.
To enter snail mail sweepstakes you need a few more things. Envelopes. Stamps. Index cards. 3x5 papers. And I highly recommend a subscription to Sweeping America http://www.sweepingamerica.com/ This is a weekly sweepstakes newsletter and because it's weekly, new sweepstakes can be published very quickly. In the event of daily prizes, this can be the difference between winning and losing! So, I highly recommend it!
From there, it's up to you to decide how much time you want to spend on entering. I won when I'd mail 10 entries a month, but my wins were few and far between and usually very small.
Also, keep in mind, it often takes time to see results from this hobby. The rule of thumb used to be six months, but I think it's probably less than that now if you consider instant wins as well as how many win notices come by e-mail these days. But, if a few months go by and you don't see a win, you can't get discouraged if you actually want to win. You need to be persistant.
Not everyone is cut out for entering sweepstakes hard-core. And that's okay, we all have different personalities. However, there are some sweepstakes that I think are worth it to the person interested in freebies to enter because if there are a huge number of prizes, that increases your chances of winning! So, in the cases of those, I would recommend everyone be persistant in a few sweepstakes with lots of prizes because after all, who doesn't love freebies, and who doesn't love them more when you WIN them?
Finally, if you are a winner, being polite is nice. If you're on a trip win where you interact with sponsors, don't get together with a group who enter regularly and discuss other wins. If you win tickets to a ball game where the sponsors will see you, don't wear a t-shirt advertising a competitor's product. Thank you notes are a nice gesture, even if sent over e-mail.
Sometimes those of us who enter have a bad reputation because sponsors think we just want things free. But we are also people who buy products. I actually switched brands of bread because they have so many giveaways. I figure why not support a company who gives so much stuff away? I've tried new products because of winning. I won some Laughing Cow cheese once, and I'd never had it before. I have some in my fridge right now because I loved it! I can many times tell you who sponsored giveaways. They do it for advertising, and it works!