I used to be a high roller when I was in my 20s. I mostly played blackjack, but I did play some Texas Hold 'Em poker when it first became popular. For me, the free food and accommodations were nice, but I was only there for the game. Blackjack has such low payouts that a high roller needs to spend hours at a table to make good money. I'm playing the house, not the other players.
The reality is that a lot of high rollers don't live glamorous lives. The good ones are definitely comfortable, but to a high roller, gambling is just like going to the office or the factory. It's what I did for a living, nothing more. That's actually one reason why I got out of the gambling scene. Doing the same thing over and over again for hours at a times at a gambling table was just as mind-numbing as watching pieces getting pushed out of a machine in a factory.