Would you check the flop in this position...if you knew you would get a bet on the flop, if not on the turn?? I will post the results of the hand, after a few replies have been made.

Table '14496182 273' Seat #6 is the button
Seat 1: bigslick886 (53936 in chips)
Seat 2: Green Egg (90146 in chips)
Seat 3: sam12 (292662 in chips)
Seat 4: hempboy420 (12683 in chips)
Seat 6: Chance77 (37880 in chips)
Seat 7: WillieWink (27854 in chips)
Seat 8: phillip_339 (86791 in chips)
Seat 9: oilerfan94dm (36542 in chips)
WillieWink: posts small blind 1500
phillip_339: posts big blind 3000
*** HOLE CARDS ***
Dealt to phillip_339 [9c 8d 9h 3c]
oilerfan94dm: folds
bigslick886: folds
Green Egg: calls 3000
sam12: calls 3000
hempboy420: folds
Chance77: calls 3000
WillieWink: calls 1500
phillip_339: checks
*** FLOP *** [5c 5d 9s]
WillieWink: checks
phillip_339: checks
Green Egg: checks
sam12: checks
Chance77: checks

Are you kidding?
Pot it, checking is atrocious.

Pot bet the flop. You don't have the nuts so don't let anyone try to outdraw you for free, even if they're trying to draw to 4K or a bigger boat.

If Sam wasn't there, it would be a decent time to check, since the pot is large in relation to everyone else's stacks. It would be easy to get it in on a later street.

As it is, especially with five people seeing the flop, you don't want someone to spike their overpair for free. Bet 1/2 pot to encourage any 5 to call. Betting pot is OK only if you have a very aggressive image. Otherwise you're letting people off too easy.

There is no good reason to check this. Someone holding a five is going to call. You might get someone holding a bigger pair to call with his two outer.
Potting it might cost you bets if someone does hit the 5's full, so you may want to peddle your hand a little by betting less (you should have a feel for a number from reads that we don't have).