My story's not a family member but a long time friend.
He bought an apartment with a nice view and lived in it for about 10 years.... so far so good.
Then he bought 10 acres of recreational land that he's owned for about 20 years now, paying an interest only mortgage, he visits it about once a year to see if it's been burned in a fire etc... It seems pointless to buy and hold it but his call.
Then he bought a house in the super expensive city that we live in, he kept his apartment and moved into the house but said this and that was wrong with it (bath tub facing wrong direction, stupid S*** like that) At this point it all started to look very sketchy as he has a business in an industry that was/has become obsolete due to technology.
He still owned the apartment he lived in for ten years but it was empty now.
So he then for some bizarre reason, after owning this very expensive house for less than 6 months he bought another one! In a very very expensive part of town! and moved into that.... now leaving his apartment AND his first expensive house empty + his 10 acres of rec land sitting idle.
Then for god knows what reasons he decided that this house too had problems, the windows didn't show off the view... the kind of stuff that, ya know... you look at BEFORE you lay your money down.
Then...(drum roll) he rented a huge house on the water front on a street know as billionaires row! AND left this 2nd house empty!!! For about 2 years until something happened with the bank and he had to sell it.
So he rented out the first expensive house to the realtor that sold that 2nd expensive house for him, the rent he charged her was a token amount as he'd let the house go and refused to spend a cent on it, water poured into the bathroom when it rained simply because he'd never cleaned the gutters, and then had his elderly parent live in his apartment for free!
His business loses money hand over fist, so he borrowed all the equity he could from the banks on the properties he had/still has, and this city was in a crazy fast rising market here. And used all he could borrow to prop up his business and live his inflated life on billionaires row.
Now his business was housed in 2 adjoining commercial properties that he'd also bought. Buying them was a savy move and he'd done well from that decision.
So when the banks wouldn't lend him anymore money, he then went to private lenders... at one point he had 1/4 million dollars at credit card interest rates! It was shocking just to know it, never mind to be in his shoes.
The private (break your legs) lenders reached their limit, so he sold one of the commercial buildings in order to prop up the business that loses thousands of dollars every month.
It's like monopoly in reverse!
His accounting is a massive mess, he owes the taxman hundreds of thousands, his office is a joke amongst his employees as it's like a hoarders nest.. you can't get in the door hardly, it's just junk and boxes pile high.
I told his relative I was concerned about him, that it was almost like he needed intervention same as an alcoholic or drug addicted person would. But his relative is a bit 'odd' to.... So it goes on, and probably will until the kitchen silver is the last thing to be sold.