Personally, I’ve yet to give money to an online poker site. However, I have considered it for a while. At Pokerstars, enter the 27-45 person sit&go’s and try to get your play money account up doing that. If you manage to finish in the “money” after a while, and you are able to honestly say you played everyhand the right way and successfully avoided being on tilt, I may make the move, and give them the minimum amount allowed for whatever method you choose to use to send them money.
You must be able to have a basic outline of hands, and quickly be able to decide whether or not to play them, when to raise (i.e. what position you’re in and how much to bet accordingly). The key, in my opinion, to playing with real money is to know what to do and when, and rarely have say afterwards, “I can’t believe I did that!” (Unless you did it intentionally and you knew it was an oddball / wrong move.)
If you know poker, have done your homework on hold’em…play a few not too too many play money sit n go’s, so you don’t pick up bad habits…you might be ready for .01-.02 ring games.
Dont judge your reddiness on your performance in play money. It is very different. I started with just $1 and I play the lowest limit tables and I have won over $17. Again, do not judge how ready you are on how well you play with play money. judge it on how you feel about how you play. You will know if you are ready, and just to test it out, throw a couple of bucks into your account if possible. Remember though, at the lowest and pretty low limit tables, people do play crazy like they do with play money so watch out.
you just need to have the confiedence to play and play for some money that you can afford to lose just incase you come up on the short end of the stick.
You can learn a little bit about how good you are playing w/ play money but real money is a whole different story. But who cares 50 bucks is 50 bucks. For example… You sign up for a $1 hold-em NL tourney friday night @8:00. You make it about 2 hours in and get bounced. Well you just had a good time for 2 hours for 1 freaking dollar, you got about 150 hands of experience risking only one dollar, and hopefully you learned a couple new things you didn’t know before. You can’t play 150 hands in a ring game learning unless your at .02/.04 limit and you still might not be able to.
 think if your serious about poker than your ready to start at penny tables
work your way up to better compitition after that if you find the penny “slots” to boring.
Tourney are fun and so on, but they are just that. With 100-10000 people to beat there is a big chance that atleast 10-20% of them will be better than you. I know it’s chep fun, but it is much more fun busting out guys at the ring tables. So I would say, if you want to make money playing poker, don’t go for tourneys, play ring games instead. You will not get rich this way, but you can make a steady income.
Start off by playing Limit holdem instead of No Limit. Get a feel for playing with real money.
Set goals and keep meticolous records. Log every hour every cent.
Know when to quit. Tomorrow is an other day.
What you really need to think is what am I trying to do when I play for money?
Are you trying to win money or are you trying mainly to have fun or are you trying to get better?
Does the bank roll that you put in mean anything to you or not ie can you afford to lose it and reload without it affecting your financial situation?
Unless you are playing purely to have fun and losing 50-100 will make little odds to you financially - then you need to a certain degree to respect your bankroll. I will say more on this in another post but simply focus on playing games where you have a reasonable chance of making a profit rather than a loss - so play to your strengths and make long odds the exception rather than the rule.
Now how do you know when your ready? - firstly I dont think free limit games are much use at all but tournaments do give you a reasonable chance to play against some quality players in later stages. I would say before you play real money buy a couple of books such as Brunsons super/system. If much of the advice in these books seems familiar to you already then that is a good sign you are ready for money tables also as lots of people follow the advice directly (or third hand via net forums etc) it is good to see where some of your opposition are coming from.
Finally all i will say is at low limits money dont expect the standard to be high - you will meet some class act players but most are awful dont treat them with too much respect.