Woot! I joined the club twice in the last three years!
For full disclosure, I own both of my houses outright. One I bought in cash, the other I bought with a mortgage and paid off in just over a year. I was lucky enough to sell a startup, so this was not a hardship nor did it require the kind of long-term dedication and perseverance that others have shown here.
When I was a teen, my family had our house foreclosed on. This certainly makes the entire notion of owning a house an emotional issue for me, and I did NOT approach it in terms of optimizing financial outcomes, or the return I could have gotten from that money. The first house is the one I live in with my wife. The second one is a house I bought for my mother, and the family, in our hometown. I was optimizing for peace of mind, and minimizing my monthly expenses -- aka health, resilience and security.
I knew the math -- I can guess how much I would have made had I put it into the market over the last couple years, WAY more than the 3.X interest rate on the two loans would have cost me in that time. Would have recovered a chunk of the taxes I paid on that income, and it would still be growing now, faster than the market value of the two houses.
I knew it would add a year or two to my FIRE savings schedule. But, I was planning working for a several more years anyways to ensure my team was established in the new company, and apparently to also build a new team and a new product! Lastly, the golden handcuffs made it worthwhile to stick around.
It also made financial sense to diversify into real-estate, since all of my deferred compensation would be in stock. Really tho, I don't consider the houses an investment. I do consider it a diversification and risk mitigation -- and it comes with a pool! Had I kept that money in the market, I would not get the diversification of assets. The risk it mitigates is losing my income, our monthly nut, with both houses, is now smaller than DWs educator earnings.
I don't get the same satisfaction from looking at my VSTAX balance as I do from waking up in a house I own outright, and seeing my mother's face when she knows that she has a home for the rest of her life to enjoy with the grandkids, and that it can be passed down to them without a bank involved, and with only property tax and insurance to keep up with. I'm going to set up a trust to handle that soon.
I know that the value of that to me is significantly higher than the opportunity cost. That's why I did it.
There is also the value of not having debt, in terms of flexibility in how I live, where I live, and how I spend my time and mental energy. Those are very valuable to me, and directly relate to my mental health, and thus my physical health. My sensitivity to that may well be a result of the childhood trauma of losing a house, but it is part of who I am. Hah! I guess I'm doing some exposure therapy for that, with the short mortgage I had, and now I am opening a HELOC as a supplemental emergency fund.
Anyways, that's why I was so happy to join the club, twice 8^)