"My dad had his own company and someone told him it made financial sense that instead of paying himself wages, he should take out a loan from his company. He built up debt for three years, while working full time, rather than paying himself. It had all sorts of bad tax effects. Like he was required to pay interest on this, which was then taxed as profit of the company, then he paid himself again paying income taxes. It took him about ten years to get out of that hole.

Then he needed to sell his house because it was too expensive. But the buyer got cold feet on the last day before the sale. Rather than having the buyer pay 10% of the price to get out of the sale he gave him an extension without an end date. The buyer then took 2 years to think about whether he wanted the house.

All the while my parents needed to keep paying the mortgage and couldn’t sell the house to anyone else because of the contract they had with that guy. Brought them close to bankruptcy. I’ve personally paid a couple of hundred a month to let them pay for the mortgage during that time."