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A 60-year-old man sold the four rental homes he'd spent 20 years managing for a combined $1.4 million after deciding the maintenance calls and tenant turnover were no longer worth it. His daughter, who's getting married next spring, says a sizable check from the sale would be "the least he could do," especially after her future in-laws offered to cover most of the venue.

The more immediate issue isn't the wedding—it's that a $1.4 million property sale rarely translates into $1.4 million available to spend. Taxes, transaction costs, depreciation recapture, and any remaining mortgage balances can significantly reduce the amount he actually keeps. Before deciding how much, if anything, to contribute toward the wedding, he needs to know what he's truly working with.

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