jamcain, others it actually makes me feel a little better hearing these stories. My parent's finances are also shakesperian in scope. Parents were working class, worked up to upper middle class, Dad retired early, but then drove himself crazy being at home with nothing to do, so took money out of retirement accounts, sold restaurants that provided monthly income, and invested in a couple investments, one which failed, the other the investors ran away with 100's of thousands and then declared bankruptcy. Dad forced to go back to work. Somewhere around this time parents divorce, Mom gets the house. Actually a good asset, back in the early 90's worth 225, 250K with 20K left on the mortgage. Idea was she could sell the house as it was only her living there (4 bedroom, 2 1/2 bath in expensive neighborhood) that she could live or invest that money.
Mom still working part time, pays off mortgage, house appreciates even more.
Dad works his way out of debt, has someone invest in a business with him, does well enough he can buy other investor out and has his own business again.
Then in early 2000's things hit the fan (2004 or so?). Mom's house is valued so much, we are urging her to sell! and retire. Houses on her block selling for 500, 600K. Instead she feels so rich she takes out a heloc, starts spending her equity. Also progidal son moves back in with her, a complete leech.
Dad is wondering why people aren't going out to eat so much, restaurant not doing as well. We (his kids) urge him, just sell the restaurant and retire, you would have a good income between the proceeds of that and soc security (he didn't take until age 72). Instead he decides to double down, borrow money to open up another restaurant which is a white elephant with high operating expenses, lease. Housing bust occurs. Restaurants are closing left and right. Because of high operating costs the 2nd restaurant closes, but he cannot find someone to take over lease so he is on hook for paying lease every month. After a year force to sell original restaurant to pay off debt. Also lost his townhome as he borrowed money from it to pay for business debt.
My Dad did not have the retirement he envisioned. But at least has social security and still works part time and so can make it in his little studio apartment.
Mom retires a 2nd time. Each time she retires, cashes out her pension as a lump sum. Instead of using pension proceeds to fix house and sell, spends it on living expenses and then taps heloc for more money. He ss is 550 a month, but her property taxes alone are 7K a year. No basic maintenance on house as "she can't afford it." Also this year she also filled out paperwork to put off paying property taxes, but will have to pay them, with interest (5-7% a year?) at the time of sale. At this time, she still has enough equity to sell the house and downsize to either small house/townhome or rent, but that window is rapidly closing.
My mother since she has retires, sits around, pays for everything for my brother (including premium cable and Xboxes), yet does nothing towards selling house, as every option she deems as beneath her and also my brother doesn't want to move. WTF? It honestly keeps me up at night what she is doing and will soon be both without any money, or a place to live, but she seems unconcerned.