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What about 99. What if he's 16/8 and you have TT?

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Some things that I'm not really certain about along these lines are like...

If I were to run a sim on his range, do I have to be 50 or more?

What is position and initiative really worth as far as pushing a non-existant edge. A good example would be your TT against a 16/8 there. TT may be like 45% there. Will the blind money, position and initiative make up for the 5% deficit I have there?

I just don't know how to answer those.

I guess things like this come into play:

Will he call down with an A UI?

Is he a fit or fold?

Is he tricky with semi-bluff c/rs?

What does he think of me?

Probably a bunch of other things I'm missing as well. How low I can go against his range answering these questions...I don't know. I guess after he raises, there are about 3 sb in the pot, and I'm investing 3. On Friday, a 2+2er opened from MP3, and I 3 bet with a pair of 3s with tighties in the blinds. I figured I was probably in the upper 40s there. I'd like to hear more conversation on these lines for sure.