Earlier quoted context omitted.
Very large and unexpected things do happen. About 10 years ago, I ended up with about a $60K bill to correct a chimney that was basically collapsing and pulling the house down with it. But I agree with your general point. In the case of my paid-off house, I figure it's about [EDITED] $1K per month (counting some big projects) for upkeep (depending on how you count things that are nice-to-dos rather than strictly nece…
That should be covered by homeowners insurance, at least in part. That your old crumbling house was under-insured is no argument against homeownership in any way shape or form, just an unfortunate anecdote.
That kind of thing isn't covered by most insurance unless it is caused by a covered kind of event, and the additional cost of insurance to cover it would, of necessity, exceed the expected cost without insurance because insurance companies need to meet all covered costs, plus administration costs, plus turn a profit.
Insurance makes certain costs more predictable at the cost of making them more expensive.