1. Availability
Some sites are not available in all countries. Currently, Titan Poker and Party Poker aren't available in the US, while Bodog is not availale in Canada. Furthermore, the all have certain accepted methods for deposit and withdrawal. Ensure that you can move your money around. While I don't guarantee it will be quick, it should be straightforward and reliable.
2. Size and Features
I think most experienced online players would tell you first of all, it's about the poker. Where can you find the games you choose to play, at the times you choose to play them? How is the competition? What are the perks? Is the software pretty and useful, or offensive and hard to use? You should be able to download and sample the software without too much time investment.
3. Deposit Bonuses
Virtually every site has a deposit bonus for first-time depositors. The thing is, most will also not release the bonus until you've played enough hands to cover a certain amount of rake. Know this, cash games generate much more rake, so players who play cash will "clear" a bonus much quicker. So before you pinch to put $400 in to play $10 SNGs, realize that it will take hundreds of SNGs to work off that bonus. It's very possible you won't see very much of the bonus $400 at all.
Alternatively, Bodog is one site that offers an instant deposit bonus, 10% of your deposit currently. In this case you get a much smaller amount, but receive it instantly. No hand-playing requirements.
4. Rakeback/Referral Bonuses
One more choice to make is who you are going to reward for introducing you to a new site and making your first deposit. There are oodles of choices. An important thing to remember, no matter what you choose here, it is separate from any Deposit Bonus you might get. Usually you get 1 of each, if you are savvy enough to make sure you get a referral before just signing up and depositing.
Some blogs will have referral codes, and you can reward your favorite blogger by using their code when you sign up. Not me personally right now, but if you love me that much, drop a few bucks and join me in a HORSE tourney ;)
Some sites will have other offers, such as twoplustwo.com. They will offer five or six of their best poker books if you use them as a referral. They are an awesome site that truly does have a great poker library for beginners to pros. I could easily recommend twice that many of their books.
But, I saved the best for last. Rakeback, aka rewarding yourself.
Rakeback is something that is offered by several sites, and boils down to this. You play X amount of poker, and Full Tilt makes money by taking $Y in rake from pots that you win. These sites will give you a certain percentage of $Y back at the end of a fixed time period, such as each month.
One such site is http://www.ThisIsTheNuts.com. With offers for over a dozen poker rooms, you can follow simple directions to sign up, and that's it. Whatever you pay to play poker online (the rake), you will now pay a significant percentage less. Up to 25 or 30%, or maybe even more. Free money.
The essential step to enable rakeback is using the rakeback site's referral code, so that the poker site knows you were "referred" by the rakeback site. Which means you cannot use any of the other above referral options, or any other unmentioned ones. Make sure you do this correctly though, because it's the one part that MUST be done right, or it may invalidate the whole process.
It may seem like, "what's the catch?" But the referral, combined with the fact that any rakeback paid out is only a percentage of rake generated, and you should be able to see how this could be mutually beneficial for everyone involved.
So, the choice is yours. But if you are going to be a serious player, rakeback is the only sensible option. It will pay you back over time, and money is the best gift of all.
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Go get 'em! Or, I also highly recommend the play-chip route. You can create an account without depositing any real money (although you may want to check on the referral requirements, they may need to be filled in when the account is created). Then you can go play for free, against other real players. Be careful, until you get a balance of millions of play chips, you can't truly get a sense for the competition out there. But, that being said, there is a level of competition right for EVERYBODY out there, it's just a matter of stakes. If you are completely new, maybe try $0.25/$0.50 Limit Hold'em, or a $2 Sit 'N' Go.
Whatever you do, have fun! And come back here for all the strategy you can eat, once you've made the choice to start conquering the game.
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