> Is it easier or harder to afford basic foodstuffs?
Processed foods are far easier to afford, but they are extremely unhealthy. As for other basics, many have gone up over the last 50 years.
> Do they eat out (luxury) more or less?
Women now work. 50 years ago they did not. Less time/people to cook at home. Not like everyone is eating at steakhouses. They just don't have the time so they go to Chipotle or McDonalds or Panera.
> If they own a home, is it larger or the same size?
Most people own legacy homes-they are the same size because they are the same homes. New builds are building bigger houses but what "regular" person builds new homes?
> Who has better healthcare?
This has more to do with advancements in medicine and technology than people becoming richer.
> Who spends more on entertainment? How much do they spend on the family pet? Who spent more time furthering their education?
Furthering education is largely on credit, so this is a bad measure.
> and the modern "regular" person would be wealthier in every one of these categories.
Nope.
It's impossible to separate people becoming richer from advancements in technology. We didn't grow GDP by 77 times, because we work 77 times harder.
Improvements in underlying technology are what help us create more wealth. The problem is that the new wealth being created and benefits of that new technology is being shared so proportionally.
Try to do that today in the same area. The foremen at the same sugar house could never afford a regular residential lot, much less the a house to put on it. It would take them 20+ years to save the money.
Is it easier or harder to afford basic foodstuffs? Do they eat out (luxury) more or less? If they own a home, is it larger or the same size? Who travels more? Who has better healthcare? Who spends more on entertainment? How much do they spend on the family pet? Who spent more time furthering their education?
All of these are measures of wealth, and the modern "regular" person would be wealthier in every one of these categories. And that's not even factoring in advances in technology that make the quality of life of a person better even if there share of societal wealth goes down.