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I would absolutely not lower your prices for anyone, especially not local high profile bankers. You don't want it known that you will bargain, and it sounds like these folks can more than afford it anyway. If they can get your portraits for "cheaper", that's the psychological value they'll put on the end product.
As far as size, I don't like to do head sizes that are less than 6 inches. It's really up to you on that point. Tell them how you like to work.
If you act like a serious professional with requirements and limits, people will treat you like a serious professional. (Like Peggy Baumgaertner always says: "fake it 'til you make it.")
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