Re: OESD + flush draw OOP 50NL
The reason I don't like check/calling this turn is that it puts you in a bit of a tricky spot on the river. If you make your hand and lead on the river, your opponent is never raising you even with a set (unless you make the flush and he makes the nut flush), so the probability of stacking him is 0% with this line. To have a shot at stacking him, you would have to go for the checkraise, but an A, 9, or club will be sufficiently scary that he is probably only going to bet a 2 pair or better made hand (as well as perhaps a few bluffs), and may even check back some of those.
For that reason, I like leading the turn better. With this line, you will fold out many marginal one pair hands (which might have still won the pot had the turn went check/check and they decided they could call a river bet), and you will still stack all his sets and two pair hands, since these hands will almost surely raise you on the turn, you will call, and if you hit the river you will open shove when 95% of Micro Stakes players will crying call you even though you are not exactly doing your utmost to keep your hand mysterious at that point. Aditionally, you will guarantee yourself 2 bets against all his good one pair hands like top pairs and overpairs.
Checkraising the turn is real good as well, but it will surely create some tricky river spots you need to be ready for. For instance, what happens if he calls your checkraise with 54 of clubs, and the river comes 7h. Now do you shove and get him to fold or do you check/fold and let him bluff you out of the pot with 5 high? Or it could come 5h on the river and go check/check and we would be super embarrassed when he won the pot with that 5c4c, or maybe even beat us with an Ace high flush draw of his own! But then think about how stupid we would feel if we jammed those same spots and he decided to call with AQ or AA!
So, all in all, in the interest of avoiding these crazy river decisions I think I would slightly prefer leading the turn.