Lottery Winner would buy what kind of Stereo Gear

You meant to say systems, didn't you Rleff? I would set up at least 3 systems, Horns with SET, Ribbons/Planars with Solid State, and Dynamic with Tubes. Certainly each would have it's own custom designed room.

Nothing would change. Why should it? This is a never vending quest. The big leagues just might end up being the minors, though.

"Some of my favorite artists: Sinatra, Miles, Holiday, Rubinstein..."

You can live in the past or explore new artists.

"You can live in the past or explore new artists"
Yeah, but that is a free choice.
Not a valid criticism.
The fact one can explore nearly endless old music, is just as valid as chasing all over Hell and back listening to 'new' music.
Making the mistake of thinking what you want is the best for anyone else?

One of the problems lottery winners have is the inability to enjoy old pleasures in the same way they used to. They often wind up less happy. If I had the ability to assemble a "cost no object" system I'm not sure I'd enjoy it more than my relatively modest but personally tweeked system that gives me so much pleasure now.