I started on play money and did something similar to what your proposing.
You sound like you're quite serious so this is what I recommend:
1] move to the 0.01/0.02 at UB or
Pokerstars by depositing $100
2] Buy Pokertracker ... = $55 - this is used to analyse your game
3] Play 10k hands then post your stats from pokertracker here.. There are ppl who play NL here (e.g me, missot Bonch), Omaha, and Limit (that's the one without the slider bar).
4] I would advise against playing tournaments simply because it is very hard to analyse your game. In ring your averages mean more. Once you master ring, tournaments are trivial.
spend some weeks here posting hands and asking questions.
If you must, post some of your bad beats..... but I ain't going to read them - they happen.
I started on $1/$2 play money a couple of years back.. Six months ago I played in ( and am now comfortable at) $1/$2 real..
On the internet there are no lucky players. It is easy to play 20k hands a month on the net. Statistics bite at this work rate - i.e on the internet you are either a good player - or a dead player..
Best of luck
Bob