Is this still possible today? From my experience, it seems very expensive to buy original art (that isn't prints). Just materials cost tends to make decent sized paintings $500+.
It's hard to be a working-class collector when there are a lot of upper-middle-class people who just want decorations for their walls.
Very much so... but don't forget, you have to fish where the fish are. They collected in NYC, an environment which facilitates art collection- many artists move there. It also appears the couple had no children?
If you're looking for good, cheap art, try looking around in a town which has a small art school. They always have graduation show and students work very hard on those pieces. And if you're interested in the valuation of art, be sure to attend an art history class.
You could easily liken it to being angel investors in Silicon Valley. A middle class couple might become great at it, but they wouldn't be able to pull it off in Sheboygan.
It's hard to be a working-class collector when there are a lot of upper-middle-class people who just want decorations for their walls.