First of all, a little update on how things are going. I officially broke out of my downswing a week ago by winning a little over two racks in the Oaks 30 game. This put me at 3.5 months of break even poker. The next day I won about 6 racks in the Bay 20 and was happy as a clam. On the next 3 days in a row I suffered 4 figure losses and am now just about back to break even for 3.7 months. Yesterday I did win about a rack in the Bay 20 game, so things aren't all bad. I think I've regained some confidence and am successfully reverting to a more "tight is right" preflop strategy, not because I'm 100% convinced that I'm making losing preflop plays, but because while those plays might show a small positive expectation, most of the time I make them I get into really tricky spots that end up putting me on tilt after I screw them up. As an example a fish open raised and somebody cold-called, and I called two on the button with King Ten suited. This is very marginal. If I play like a God post-flop (which against these guys isn't that much of a stretch) I probably stand to show a small profit. But when the second guy limps in with aces, I flop a flush and the 4th spade hits on the river to give him the lock down nuts, I tend to tilt a little. So for now, tight is right.
Now for some actual content. A fundamental problem exists in mid-stakes limit hold 'em games when you flop a strong flush draw, and that is the following:
1. If 3 or more opponents call bets, you are making (large amounts of) expectational money.
2. If 2 or fewer opponents call bets, you actually have a chance at taking the pot down unimproved.
Part 1 is pretty easy to understand. With a strong flush draw, such as Ace Queen with one other broad way on board (to give you some chance of making an ace-high straight), even when up against top pair, a straight draw, and black aces, you have about 39% equity. With weaker flush draws your equity against your opponent's ranges is worse (mostly because some non-zero percentage of the time you are drawing virtually dead against a higher flush draw), and of course if someone flopped a set you're in worse shape (as they have immediately killed one of your outs and have a pretty fat re-draw to fill up if you hit on the turn), but the long and short of it is that a flush draw has somewhere between 30 and 40 percent equity on the flop. If two people call your bet, you're probably making a little bit of money. If 3 or 4 people call, you're making more. And if 6 or 7 people call, you're printing the stuff.
Part 2 is also easy to understand. Given that you have a flush draw, it's pretty difficult for other opponents to have draws (obviously this depends on board texture and your opponent's preflop ranges), and therefore once there are more than 1 or 2 of them it becomes pretty likely that somebody is going to show down their hand against you. Now if you actually have ace-high sometimes this is ok, but with weaker flush draws void of showdown value this is a pretty serious problem that leads to rampant triple-barreling with jack high.
The problem then is how to balance these two contradictory goals. On the one hand, you'd like many people to call your bets. For example, if you know to a moral certainty that a hand is going to showdown and all you have is a weak flush draw with 33% equity, you'd prefer that 3 opponents call a single bet (netting you .08 bets of profit) than that only 2 call a pair of bets (netting you zero bets of profit, as you had 33% equity but 33% of the bets that went in came from your stack). But you can never know to a moral certainty that a hand will go to showdown. I have seen some preposterous turn and river folds in the games that I play. 4 people go for a cap on the flop, then one check/folds the turn closing the action getting 12 to 1, and the other two mysteriously muck the river, inevitably mumbling something about a straight draw and refusing to chuck $40 into a $600 pot. So then, what do you do? As usual the answer is "it depends". I don't claim to have all the answers, but here are some things I think about.
1. How many opponents are left? Once you get above 5 people calling bets you're basically in the right to shovel bets in hand over foot. But with 4 or 5 sometimes it's tricky, and with 2 or 3 you might want to play passively against incredibly showdown opponents. Which leads to....
2. Are any of your opponents very show-down oriented? For example if I'm in a hand with another two plus twoer who has little history with me but respects my game, he will probably call me down a little light because he will be a little scared of getting outplayed. I used to call Pete down super light, but have fixed most of that leak (he still outplays me all the time, but I'm just no longer frightened by the concept). Tough show-down bound opponents suggest passiveness. Fit or fold tag-fish who can be blown off pairs, on the other hand, demand raises.
3. Location, location, location! What is your position relative to the preflop aggressor? What is your likely position against the source of the likely turn bet, both if you hit your flush and if you don't? How many players have already called the flop bet, how many more are left to act, and are those players likely to call two cold with bottom pair? It's important to remember here that you're really not trying to protect your hand or clean up any outs. Unless you can get everybody to fold, you're gonna need to hit to win, and folding out a guy with one pair usually isn't that critical (since somebody else usually has a pair that rates exactly as well against your no-pair).
4. Would you take a free card? One thing that's important to note is that playing flush draws passively in position often results in getting an extra raise in on the turn the 20% of the time you hit right there. If someone bets out from the small blind, two opponents call, and you just call with a flush draw on the button (most of the time I'd raise here, but I'm playing devil's advocate), you'll often have the turn action go bet/call/call when it gets to you on the turn even if you do complete your flush. If you raise, however, you might be able to take a free card on the turn. On the other hand, a few bad things can happen. The initial raiser could 3-bet, knocking out the other two players, and then lead into you on the turn anyway. All of a sudden you've put 2 more big bets into the pot as a substantial underdog (something like 2:1) when you could have gotten to the next street for just 1, with potentially even more padding from the players caught in between.
5. Overall strategy concerns also often come up. Being known as a player who fast-plays draws has advantages. Specifically, if you play a set of 5s the same was as the jack high flush draw, your set of fives is going to start getting looked up by ace high, which is obviously awesome.
So what are you actually supposed to do? After writing this post I've realized that I play my flush draws pretty passively a good portion of the time when I'm not the preflop aggressor, mainly because I've seen time and again that it is a truly herculean task to get ALL of my opponents to fold without showing down their hands. I think I need to look for more spots to put in raises with flush draws, not only to attempt to win more pots, but also to fit in with point 5 above and make myself harder to play against.