First off, let me preface a lot of this with some basic defenses/admissions: I realize my approach to playing poker (in terms of how to most quickly obtain a self-sustaining BR) are far from the "safe" route... I know I've made mistakes and such, and I know I've done the "oh, another small deposit of $50 won't hurt" bit one time too many...

That being said, I think I have considered my approach until now to be mostly exploratory. I first started playing poker online at UB about a year and a half ago (July / August '03) ... but I stopped very quickly after I slowly worked my initial deposit of $30 up to $120, playing 0.25/50 limit. I think I even played some 0.10/0.25 NL with this small of a BR... I know once I hit 120, instead of doing the smart thing (withdrawing my $30 as profit, and continuing playing at low stakes), I decided I was ready to play some serious NL, and that was the game where I was better, dammit! Since, of course, I could represent bigger hands, without actually having them... a few all-ins later, and my 120 was down to $40 ... and it trickled down and down. All this happened after about a month and a half of play (at this point my only poker book was Hellmuth's Play Poker Like The Pros

So I decided to take a break. For several months, I didn't play any poker, though in the interim, I did acquire a few more poker books - a few Sklansky standards and Lee Jones' Wiinning Low Limit Hold'em, which I tried to study, but didn't do a great job at, since I was so fixated on my NL game. Then, one night, at random, almost a year ago, I decided to put in "a few more dollars" and play for a bit. Well, I continued to play 0.10/0.25 NL - and got my ass whipped again, on an all-in. (I was even so amazingly bright as to have had a few beers while I was playing, and figgered, by *gawd*, that my JJ must be good! .... sigh... if only I could slap that version of me back then.)
So I decided I'd quit for good. No more poker. But of course *that* changed. Fast-forward to about December-ish of last year... I wanted to get back in the game I enjoyed so dearly. So I figured I'd deposit some 'healthy' money (only $50, when my 'BR' was down to a few dollars, I think), and played a much more tightened-up version of my NL ring game of 0.10/0.25. (Yes, this was still a big mistake - although in retrospect, I'd still only been playing for fun, even though I didn't relish the idea of continually having to squirrel more and more chunks of money into UB, while not really boosting my BR.)
For an off-and-on period of 2 months, I would alternate in a cycle of depositing some money, winning some money, and losing some money, until I finally had it and deposited $100. At this point I had realized I was in over my head trying to play a $25 buy-in NL game with only 3-4 buy-ins' worth of BR. So my BR was somewhere around 150, and, as luck would have it, I started my first foray into lurking at BTP - where I read some interesting articles on SnGs. I decided that I really liked playing SnGs, because they gave me ability to work on my NL game, while offering a relatively low-stakes way to learn. I knew, at this point, that playing SnGs, where tourney play changes basic strategy a great deal, was not going to be like playing ring games, but at least I'd get to play NL and have some fun, and since I'd dedicated myself to proper study of the game, I was going to stand a pretty decent chance of at least being a break-even player. At this point in my study, I had really grasped ideas of pot odds and expectation, as well as basic tournament strategy ideas, like blind stealing/defense, hand selection, etc. I think at this point of my 'career', I was probably a very able student, and would have been probably a decent-enough break-even or slightly net-plus player, had I stuck to playing one game, instead of switching from limit, to NL, to SnGs ... but alas, I made yet another mistake (this one being the notion that I could 'build' - or more appropriately, rebuild a BR playing SnGs, at my skill level back then).
So naturally, that didn't work so well (playing SnGs, that is), and I put aside poker for another couple of weeks... but my interest in the game had not faded, and my determination to become a winning player at *some* form of the game had not left me. So a few more deposits of squirrel-money ($25 here, $50 there, etc.), and I was back up to $170 ... and I decided I'd settle down quite squarely and alternate play between 0.25/.50 limit and 0.50/1 limit. At this point, I *knew* that 0.50/1 was beyond the means of my BR, so I didn't play it much ... but I found that I was actually a much stronger player than I had been when I first started, and so would end up with consistently net-plus sessions. Also, by this point, I'd invested in quite a few more poker books (I think my library is up to something like 9 or 10 books now

Well, not quite. I did have some great positive sessions ... boosted my BR up to $225 ... then it slid down. A lot. To ~130 or something like that... all because of a pretty bad cold streak. And at this point, I'd figured - OK, this game is just plain unbeatable. I can't win. I suck. I have read all the damn books. I've read all the damn forums (BTP and 2+2 being my favorites). I have PT, and GT+. I just cannot win. Or so I thought. (In retrospect, I think I just did have a really bad session - and this can happen - but with all of my mistakes up until then, I wasn't willing to abandon the idea that I just plain sucked.)
Now in all of this time, I'd also been playing some live games - not for money, but we play seriously, so whatever I learned was still applicable to playing a money-game. And I found myself up in Seattle visiting a friend - more specifically, up in Seattle, near a casino - a live B&M cardroom casino - where I'd never played in before. (I live in Texas...) So I sat down at a 3/6 game (it was the lowest limit they offered), and plunked $200 worth of chips out on the table. 2.5 hours later, I had gotten up to $300, while my friend was down $200. So we left, and I was feeling great about myself - that all the skills I'd built up over the thousands of hands of play were actually paying off. (Granted, it could have just been one lucky session - but the fact that I was seriously scared that I'd lose my $200, and instead walked out with $100 more was a HUGE boost to my confidence. On a tangent here - can it really be that that playing in a B&M room is easier than playing online?)
So I came back to Texas thinking I wanted to be in more live games (the craving to go back and make some real $$ playing live hasn't quite left me, I'm afraid


I deposited just enough to give me a $200 BR at UB. And finally, I got serious about my game. I decided I would pay great attention to table selection (which I've found, has really helped my game a lot), in addition to all the other things I knew about pot odds and expectation, and value betting and check-raising, etc etc etc.
And guess what? I finally have started to win. My $200, over the last few weeks, is up to just under $400. I am excited! I have had some pretty wild days - the most amazing of which have been over this past weekend. Friday night, for instance, I started up $25, then dropped down net -$35, and was feeling miserable (though I kept telling myself it was bound to happen from time to time), until I found a better table, and quickly made a net plus of $65. Today a simiar thing happened - it was up and down and up and down, until I won a great $75 pot (at 1/2 !!) - you can read about that in the Limit forums..

Anyway. The point is that here I am, now, just shy of $400 (I think it's like $395 or something). According to the ~2200 hands in PT, I have an hourly win rate of $7.13, or 4.34 BB/100, and an SD of $30.5024, or 17.7719 BB. This leaves me with a 0.2% risk-of-ruin - so I am actually playing within my means now. And I have a nice BR starter!
Which brings me to my question. I actually tallied up all of my deposits and such, and discovered that since my initial deposit at UB, I have deposited a total of $412 over the year and a half of my online playing. This is great - this means I'm almost completely break-even after 1.5 years!! (ugh...

The question I've got is this: when do I cash out? How do I *keep* playing a consistently winning game? Is my latest upswing just another 'stroke of luck', or am I really a decent player? The stats in my PT database would suggest legitimate strength in the quality of my play.
My long term goals are not quite defined, I guess - I suppose my biggest goal is to get to the point where I am earning a decent supplemental income from playing poker - ideally somewhere like $1k/month gross. I would also like to have some BR left to play some higher-stakes multi-table tourneys now and then (like $10-buyin or $20-buyin), so that I can also work on my tourney game. My 'dream goal' .... OK don't laugh

Since I've never been in this situation before, I need some good advice from all of you amazing guys - I don't want to continue making costly mistakes and missteps. A real disaster scenario would be to move up too quickly and wipe out my now-nice stack.
Thoughts?