Houses are cheap everywhere outside of major metro areas. And raising kids is cheap if you have a stay-at-home spouse, send the kids to public school, and never fly. So basically if you recreate the typical 1963 suburban living experience, this is totally workable on (for example) a teacher's salary.
The kids are basically free (in dollar terms), if the kids go to public school, you don't fly, and you have a stay-at-home spouse who cooks and clips coupons. You also don't have to be wealthy to own property. Outside of major metros, you can get a house for $200-300k, so two houses is $400-600k and the three-unit rental building is probably less than that. And they're probably all mortgaged, not owned outright.
I don't know about the cost-of-living reality in the flyover states, but are you sure you're taking into account the 5x multiplier that kids represent for that specific example?
I think that just in terms of food expenses, having to feed five children + one spouse might be pretty challenging. Let alone if we factor in things like healthcare plans, among other things.
Another thing: the GP's grandfather was a blue collar worker, you're talking about a white collar remote worker who by definition is a high earner and not somebody average.
This talking point that things are not harder today and everybody would be able to have the same affluence of 60's people if at least they were not so demanding sounds completely unrealistic.
Food is very cheap if you eat like Americans did in 1963. No restaurants, no prepared food, relatively little meat. Rice, bread, beans, potatoes, squash, etc.
Healthcare is cheap if you consume healthcare like a person in 1963. No need for MRIs, anti-depressants, chemotherapy, most childhood vaccines, braces for the kids' teeth, etc. The big exception is labor & delivery, where what used to be standard (a long hospital stay for recovery) is now so outrageously expensive that it's not even an option.
