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at what point should someone be leaving their money in the entity and have entity paying taxes rather than passing it through to the individual and have them pay?
This is very difficult to answer in generalized terms. I agree with Clint here this needs personal attention.
There are just too many options domestically and when you add offshore options the playing field is wide open.
For clarification though, both S-corps and LLC's are pass through entities so you are taxed personally on the income whether you leave it in the business or not.
If you want to leave money in the business without a personal tax consequence, you need to either be set up as a C-corp. or use some offshore planning tools.
But selecting the point at which you leave the money in the business is such a personal issue, there is no real way to give generalized advice here.