Raise 99 in loose games?

[SaggyTTs]

So statistically, is my thinking sound? Let's say after 100k hands, I look at pokertracker and determine that certain hands win over 35% of the time. Playing games that average three or more callers per hand, I should expect to make more money by raising, yes? Or would I be better off looking at the winning percentage after seeing flop to determine raising standards?

[Evan]

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Playing games that average three or more callers per hand, I should expect to make more money by raising, yes?

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It depends, a lot.