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Sale price is a sale price. Whether you do it in cash, check, pennies, whatever doesn't matter. Now if he's looking to take that cash and underreport the sale, run. Run quick. He's already cutting out the $100k from the $300k value and he wants to hide even more. Way too shady to even consider in my opinion.
And as Sarah mentioned, your capital gains will be huge and will actually hurt you in the long run... ie: If you sell for $400k and on paper you only paid $75k, then you're going to pay taxes on capital gains on $325k even though you only paid $200k. This is going to hurt you in the long run if it works, but to me, its too high risk. Run.
WG
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