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I used to be of the mindset to pay off my mortgage when I was in my early 40's. We had a friend over for a dinner party and I was bragging on my plan to be mortgage free. This was just before the housing bubble exploded. My property value had skyrocketed.
My friend carefully explained to me the trapped equity sitting in my house that did nothing. I believe mortgage rates were around 5% IIRC. He explained how if I took out 100k of that trapped equity and put it to work making more than the 5% I was being charged on the 100K I would be money ahead.
I did as he suggested and purchased a 4 plex with the standard 25% down. We were making a little over 10% cash on cash on my investment. I had a little more cash left over that we sat on waiting for another deal where we could get that kind of return.
Shortly after the housing market crashed we purchased a Duplex on a short sale with about a 30% cash on cash return.
Mortgage money is cheap for now. We have 4 mortgages, 3 on rentals and 1 for our primary residence. The tenants are paying the bills on the rentals. We could take money out of investments and payoff the primary but as long as the investments are earning more than the Principal and Interest, it doesn't make since to me financially.
We do have 3 properties that we own free and clear or I should say our IRA's own free and clear since they are situated inside a Self Directed IRA.
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