A simpler reasoning is that there wasn't any demand for his paintings while he was alive. His show ran from 1983-1994 and he died in 1995. He was reasonably popular at that time, sure, but Bob Ross as we know him only blew up in the 2010s in the internet/YouTube/streaming age.
Now there is a trove of 1,165 paintings which are no doubt valuable, but cannot all be sold because they would flood the market and decrease their own value. So Bob Ross, Inc. is cleverly keeping them under lock and key and letting the scarcity drive prices up.
https://negosh.com/brand/54d96e91-3646-49bd-9226-53265743157...
• As people get older, their brain connections start to break down faster in midlife (around 40–60 years) because brain cells don’t use sugar as well. • Giving the brain a different fuel called ketones can help keep those connections strong during this middle‐age window. • This suggests that helping the brain get fuel in midlife could keep it healthier and slow down memory problems later on.
You can ingest ketones on their own (generally expensive supplements), but this article is more interesting in that a ketogenic diet (very low carbs) may have similar benefits.
That was a rare very good decision for kid me back then, and it's paid off ever since.