My in-laws are approaching this issue right now. My FIL was self employed for most of his working career. He had a failing business pretty much that entire time. He stuck it out and ended up hardly being able to put food on the table and shuffling around payments to the different providers to stay 1 step away from getting the utilities turned off. Obviously, retirement wasn't an option for him. He decided to retire in his early 60's and closed the business. He was probably losing money anyways. My MIL was a SAHM and helped out at the business when she could. The last 10-15 years, she's been working as a LPN at a nursing home pulling a modest wage. They are currently living off his SS and her paycheck. The problem is, they live in a nice town in NJ right outside NYC. Their property taxes alone are 10k a year. I hardly pay 10k for my mortgage+insurance+taxes living in the midwest! Basically, they are going to have to move when my MIL retires. It would have been a tough situation, but unfortunately, my FIL had a brain tumor and while it's been removed, he's not fully there. They spend money recklessly, and their house is falling apart. Their only hope is that they can sell their house for decent money. The house is a pit, but the land has value to a developer. They could tear down their hobble and build a 1m home on it easily. If they can sell it for ~300-400k, they could turn that into an annuity* and get 2k a month for life. Mix that in with SS, and they should be in decent shape.
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*I don't typically recommend annuities, but in this case I think it's a good plan. My FIL is the kind of guy that if he had access to $300-400k would blow it all in a year. I like that buying an annuity locks in the income and removes most of the risk, especially if you split the investment between multiple companies. Even if we could keep my FIL away, my MIL would probably spend more than the SWR would allow. I just don't see themselves limiting themselves to 2k a month if they have that much in the bank.