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I would never pay off the mortgage in your situation. Right now you can get something like 4.75 APR on a 5-year jumbo CD. Rates are likely to go up.

Um, I'm confused. The 5 year CD is 4.75%, his mortage is 5.25%. How woud he be making money by putting it in a CD instead of paying it off? True, you could say the mortage interest is tax deductible, but the CD interest is taxed, so that's a wash, not an advantage. He'd need an investment that's better then 5.25%, hopefully by a decent margin, to be a guaranteed advantage. Now, the market can return better than that on average, but there we get to the confort of risking it not doing so in his time frame, and his comfort level with the debt in general.
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