A little late on this reply, but it's an easy one for me to answer.
Without a doubt the worst significant purchase I ever made was when we bought a house in late 2005. Looking back, I am not even sure why we did. We had a nice 3 bedroom apt (it even had a full basement) with a very reasonable rent, but I guess we had just reached a point where it seemed like the thing to do. My husband's job paid very well, we had two small children, and I know my husband wanted somewhere with a bit of a yard and some quite.
We found an amazing Victorian brick farmhouse that was truly beautiful, and I suppose I was taken by the idea of living in such a grand looking house -- even though it was clear there were things we needed to improve -- gutters, windows, etc. What should be a law is having every first time home owner sit through a course where you learn about all the worst possible things that can happen when you have a home. They should show in graphic, gory detail about every little thing you are now responsible for, and how every single one of those things can go wrong ALL AT THE SAME TIME. Because I know I didn't consider half of what I should have when I thought about home ownership.
It certainly didn't help that the cards started out stacked against us. The owner left it in a deporably dirty condition, so we knew we were going to have a massive cleaning to do before it even felt like "our place" - and that was NOT something I looked forward to in the slightest. It was so dusty and dirty in places that we couldn't even afford to pay someone to clean it. It would have cost A LOT. (We had a few estimates.)
Then before we moved it there was a leak in the upstairs bathroom that flooded the kitchen while we were away for Christmas. So we had to move our stuff into the dry parts of the house, then live in a hotel for a month while the entire kitchen was gutted and rebuilt. A year later the water heater broke, along with some pipes, and a flooded basement and no hot water meant we spent a few more weeks in hotels getting things sorted.
And we had well water, which was disgusting, no matter what you tried to do to it.
All the complications and bad luck while we were there had me spiralling into depression, and even my husband fell into a dark mood, making it hard for him to work full time, which meant that even though we now had a mortgage that was nearly 3x our rent, he started making less money. A LOT less money.
And don't even get me started on the snakes. We had cats for a while and luckily one was a hunter; my husband came downstairs one morning to find a bitten off snake head the cat had left in the dining room, probably as a trophy. I feel queasy thinking about it even now.
In the end we defaulted on the mortgage, and because we didn't want to stay in the house, we tried to work with the bank to sell it for what we could (yes, this was the beginning of the fall of the housing market, so with our second mortgage to fix all the things that went wrong, we had more debt than we could ever hope to cover with a sale) -- but our letters were never even answered, much less worked with! So we left it about 2 and a half years after we bought it, and moved out east. At that point I felt that if I didn't get to the east coast (this was in the midwest), I was going to die. Seriously.
So what did I learn? I am NOT meant to be a homeowner. Even though I did
enjoy being the one to tool around on the riding lawn mower (I really did!), I do not like tending a garden, repairing ANY part of a building, dealing with broken appliances or pipes or wiring, or dealing with pests like mice or snakes. I want to live where all of those things are someone else's problems, and I just pay a monthly fee to reside.
I don't care that this means I have no real equity. Equity is too stressful.
Here's a slightly artsified photo of the house. Taken in winter, it makes it seem a bit spookier than it really looked, although maybe now I'm just seeing what I should have seen the first time: Nice place to visit, but I don't want to live there!