(NL400) Semi-Bluff Check-Raise all-in when board pairs

[KingGordy]

I think you do a good job of repping a J, the only problem is he's going to have a J himself a lot of the time. I'd expect him to fold anything less than trips though.

[grando]

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I think this is terrible and you get owned by 8,8

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which you still have 14 outs against

[LouisCyphre]

In retrospect I didn't like my play and that's why I posted it here.

Two basic assumptions:
He will always calls with a J or better.
He will always fold with a T or worse.

1. I risk $342 to win $152.
2. He showed strenght twice by betting the flop and betting into the paired board.
3. I don't know if he is able to fold an overpair.
4. At that time I considered it a semi-bluff having 8 outs in mind but in reality that's probably not true.
On average it's maybe 4 outs which makes my check-raise resemble more closely a bluff than a real semi-bluff.
(Against TT,JT,55 I am drawing dead.
Against the most probable J ->AJ I have only 4 outs. Same versus AA or J9.
I have 8 outs against KK and 11 outs against QQ.)

On the plus side based on card frequency it's improbable he is holding a J and I should have lots of fold equity which I really need (see 1).