re: When to pay off the mortgage

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Serious question, but would you be shocked at all if the market didn’t beat that over the next 5 years?

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Shocked? I don't know if I would be shocked but I would definitely be surprised if we don't average 5% over the next 5 years (starting from today). I would be curious if there has ever been a previous time in history where the market had already fallen 20% and then from that point it hadn't averaged 5% per year for the next 5 years. That would basically mean the SP500 getting to 4900 which is only slightly above the high in late 2021.

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Since the average homeowner moves every 5-6 years

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I believe the actual average is 7 years but I think this is also a different conversation. Would you pay extra on your mortgage if you had no intention of every paying it off? If you are only staying for a few years, you likely won't actually pay it off so you don't get the no debt emotional feeling. It really does just become a math equation at that point.

If we are seriously considering the benefit of the emotional feeling of no debt then the timeframe is probably closer to 15-20 years. That only strengthens the math in the investment side of the equation because the probability of the market gaining less than 5% annualized for 15 years is much lower than lowered returns for only 5 years.

I also find it funny that everyone brings up the returns of the last 10 years and the impact on the next 10 without taking into account the 10 years prior. Maybe the last 10 years of returns were also propped up because of the lost decade of the 2000s.

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wouldn’t it make more sense to pay down on some principal and give yourself more equity when you sell?

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If you are planning on moving in the near term, I would rather have the liquidity of money outside of home equity than home equity for buying my next house. It just allows more flexibility. I can buy before selling if I want versus having to sell first or spend money extracting the equity out of my home to put on the next home. Again this comes down to ensuring you actually invest or save the money. If the options are paying extra on your mortgage or spending it then of course the better purely financial situation is to pay extra on your mortgage.