To answer your question . . . if I were independently wealthy I would still very much enjoy playing music. I just wouldn't play in some of the same venues where I work now.
I would most likely hire three or four of the best sidemen in the world and a couple of real live backup singers. If the occasion demanded I would have a brass and reed section on standby.
I would buy the finest p.a. system that could be bought and hire roadies to haul it around in my tour bus and an engineer to handle the sound and to make live multi-track recordings of every show.
Probably most of my "jobs" would be for nursing home residents. Even though most nursing homes COULD well afford to pay for entertainment, they in fact don't and you will not find a more appreciative, deserving audience anywhere else. I'm not talking about the big-city nursing homes for rich people, I'm talking about all those little ones in small towns around the country where the only entertainment they get is a local lady playing piano and singing hymns. (There's nothing wrong with that either!)
I would also do fund-raiser shows with the proceeds going to deserving charities.
I would still have the best arranger keyboard available at home or to have on call in the back of my $50,000 van, in case I wanted to play for momma and them on Sunday afternoon.
Until all that happens, I'll keep on doing it as I am now, and that doesn't leave much room for freebies.
DonM