[mgsimpleton]

I hate check raising in that spot because if villain does have a diamond draw, you will have NO idea what to do on the turn... fire again or give up? It's tough in general being OOP with a marginal hand and that's the main problem, the turn is very difficult in that spot.

Some ways to combat that: With a loose PFR OOP and a marginal hand like 88, consider reraising preflop. Hey, you're likely ahead... and they'll be less inclined to call with whatever crap they have. In that situation, when you fire the flop you will often take it down. Of course it will be a similar situation on the turn, but as the aggressor the whole time, it will be easier to control the hand.

Consider leading the flop. If he raises you, believe him that he has a K or just live to fight another day. If he calls, fire again on the turn and check the river (many people will not bluff this missed draw because it is the classic "check and call a missed draw so if they do have a made hand they will check behind) and on those two streets it will have cost you just about the same as your flop check raise. Of course, its important that you are also leading your sets (and this board is inherently less scary for a potential two pair... basically this board just sucks with a mediocre hand oop against an aggro/tricky opponent).