His parents will die sooner rather than later—they're in their 70s and 80s and in failing health—and leave him the house. It's a good house, near a commuter train station, in a quiet neighborhood. Big yard. Trees. The Complete and Total Loser will sell it in the first spring/summer it's his as he's heard that houses fetch higher prices when the gardens are in bloom, and buy a small house far in the sticks, where the cost of living is low.
He'll modify this house so he can be off the grid to the greatest degree possible. He'll keep to himself. He'll work part time at a job in which he needn't interact with people much. Cleaning offices at night, stocking stores. This, only if necessary. He lives in a major city now on less than $20,000 a year after taxes. If his house is bought and the property taxes are low, he can easily live on less than $1,000 a month.
This is how the Loser will live. Reading, exercising when he wants to, eating simply, learning to grow his own food if his property is fertile. He'll make trips into the city every year or two until age makes him ridiculous. More ridiculous than he is. A cane, perhaps. A walker, no. He'll sit on benches in the park and watch the young run by.
When he dies he hopes it will be on his own bed, quietly, in his sleep. The few people who know him will hear of his death and say, "Huh. I thought he died years ago."