I tired writing out a long and thoughtful response but I feel like it started to not really make sense, considering what you were asking 😅
Maybe this one won't make sense or help much either, but I wanted to respond & chime in. 😊
I think, as far as painting goes, the art world is an incredibly strange place, there are loads of reasons why people buy art they don't understand (or even like) but one that comes to my mind first and foremost is: money xD
Paintings .. If you buy the right pieces are a good long term investment, some artists get so famous that no matter what they make, it will be valuable just because their name is attached to it.
At least that's my take on it.
There was a quote I remembered reading by Picasso where he was basically saying (laughing about) how, the less critics understand his work the more they praise it, the more money he makes from it. But I can't find it.. And I could be wrong... as it was such a long time ago that I read it. 😋