These situations are the ones were bluffing works best for me. You a.) have position b.) have shown aggression c.) no one wants that pot anyways d.) are not playing a tight passive yahoo e.) only special opponents will I bluff check raise f.) they are overly weak tight
Having position on the original aggressor is very helpful in that if he checks you can fire, if he makes a weak continuation bet or blocking bet you can raise. Check raising is usually futile and expensive against most people when they hold a big pair or top pair top kicker, a big pair to some of these guys is TT and they are willing to really over play it, you are also going to have to follow it up when the turn likely misses you as well. I just don't bluff them they have a gaping hole waiting to be exploited given the time.
I also try not to bluff in a pot that someone else raised, again especially with out position. They have shown an interest both preflop and on the flop, if you are attempting to push them off a hand, unless they do something silly like vary the preflop raise size preflop based on hand strength and you have a fairly accurate idea of their holdings it is useless. If I am going to attempt to bluff them, I lead at the flop take my stab, if they minimum raise, I may pay and fold on the turn, if they really raise I wait like i'm trying to figure out what they have and fold. If they go nuts and I have reason to suspect that they would never value bet like that, I might 20% of the time take your 88 much further than I should and still only be right half the time.
I have about three people that I can think of that I frequently attempt to bluff check raise outplay them when they raise in late position. I know they raise any small pair, two overs, and am willing to check raise under card flops especially if I'm in the blind. I generally let go after some thinking if they reraise and may check fold a smooth call at the turn if my hand doesn't improve to something that can beat a one pair hand. Again this is against a good loose aggressive player that is trying to raise the pot, hit a hand or push me off a hand. I haven't got to sit with either of these people in 5 months and my hourly rate has dropped
The pots I'm most likely to bluff at are three handed similiar to this situaton between me the SB and button in an unraised pot. SB checks, I lead with a pot sized bet, hopefully every one folds. I then make up my mind about who ever called and what they are likely to have and fire again at the turn or check fold. I bluff frequently if I limped in first position and only the button SB and BB are in the pot, especially if some high cards are on the flop. I happily attempt to steal small pots with any two from the button and cutoff when it isn't raised preflop and they check to me. I'm likely to bluff if I raised preflop and am the aggressor especially no more than three handed, I sometimes bluff raise junk hands out of position if I'm opening preflop, then continue on the flop. I pick spots where either I'm in control, or am not having to spend much to make the bluff profitable.
Bluffing is fun! Getting carried away with it is pretty easy though, and picking your bluffing opportunities and opponents is fairly critical to making it work fairly frequently. If you have a tight as a drum table image, you are more likely to succeed than if you are percieved as loose aggressive. After all who do you give credit to actually holding a hand, the guy that appears solid or the guy that makes all sorts of curious plays?
Ugh... I have to quit posting when I'm tired and rambling, but I am rarely motivated to put some effort into a response except right before bed.