I retired at 49 with eight rental units and $800k saved: should I sell one property to pay off another?

Melissa retired at 49 and lives on cash flow from three rental properties totaling eight units. She has $800,000 in retirement accounts, $250,000 in a brokerage, and $50,000 in a high-yield savings account. She is considering selling a New Hampshire fourplex that has doubled in value and produces $2,000 to $2,500 per month, then using the proceeds to fully pay off a Massachusetts triplex that produces $3,500 per month. The trade would keep monthly income roughly similar while reducing the number of doors and eliminating the remaining mortgage on the Massachusetts property. She plans to continue living off rentals for five more years, then sell at age 60 and fund retirement with equity and retirement accounts. The decision framing weighs lifestyle and peace of mind against long-term wealth accumulation through leverage.

"“If you are optimizing for lifestyle and peace of mind, then sell. If you are optimizing for wealth accumulation over the long term, then hold.”"

"“a safer approach” and “a smoother glide path” that delivers “freedom from worry.”"

"“The cash flow I would lose on the New Hampshire rental is almost exactly the same as the principal and interest I would no longer have to pay in Massachusetts.”"

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