What I do regret a bit is selling our former el cheapo house. It would have been a much better financial decision to have kept living there. But that was pre MMM when we suddenly discovered that we could afford a big clown house and pay cash. I regret making that decision.
If I'm remembering her situation correctly, you might have more in common with @Dicey than you thought!
You're right
@Bird In Hand, but mine wasn't really optional. If I ever get off my lazy ass and wrap up some of the loose ends in my journal, I will get to this story, but here's the short-ish version for now:
When DH and I eloped, we both had affordable two-story houses without downstairs bedrooms. Three weeks later, his dad died and we realized his mom had dementia and couldn't live on her own. We made the hard decision to sell both houses, buy something more suitable for his mom's needs, and move her in with us. What we found was a crazy beautiful custom clown house just a short walk from DH's work. Come to think of it, there is more to the story.
The house was a spec house, built by someone I knew through my dear friend, who is a badass realtor. When the builder finished the house in 2007, my friend held it open and I toured it. I stood at the kitchen island, placed my palms on the cool granite counter and thought, "This house is so beautiful. Who wouldn't want to live here?" My rational brain did the math and quickly decided that there was no way it was going to be me, as I didn't want to work that hard. I never dreamed that five years later, I'd be married(!) and buying the house. The builder didn't get an offer he liked before the market tanked, so he moved into it himself. When he finally decided to short sale the house in 2012, we bought it for significantly less than the original asking price. The kicker is that my husband's office is at the end of the street, which I did not know when I married him. I knew who he worked for, but not exactly where. Crazy!
Our clown house is not a regret at all, despite property taxes that are double what we were paying on the other two houses combined. Were it not for his mom's needs, we would never have bought it. Six years later, when we come home, we still joke, "What a lovely house! I wonder who lives here?"
When his mom gets to the end of her journey and DH retires*, we will sell it with no regrets. Happily, it has appreciated significantly, so we should be fine, despite the wicked tax bill and maintenance costs.
*Note to IRP: We're FI and I'm RE, but sometimes life hands you a curveball. DH is the kind of guy who would go nuts without enough to do. As long as we're not free to live our first choice lives, he may as well keep working. Fortunately, he really likes his job, which pays well, has excellent benefits, and very low stress. He jokes he has to go to work so he can relax.