In regards to your audio setup, I suggest your next purchase be a streamer that will both play through your stereo and offer a headphone jack. Then you can listen through a decent set of headphones. There are a number of reasonably priced streamers. My method of buying audio equipment has mostly been to read reviews and look for something used.
Why the streamer? When I, or anyone else, suggests an album, it will 99% likely be on Qobuz or Tidal. You can also load Qobuz, which is now $10 a month, on a computer as an interface. People used to tell me about albums and I didn't want to lay out the cash to experiment. You suggested Wayne Shorter and I have probably found every album of consequence he's ever done on Qobuz. Too many for me to listen to.
On to music. I went to see The Dead a number of times in the sixties when I was going to Berkeley. I have one of their albums which I don't play often. I do, however, really like David Grisman. I have a album with him and Stephan Grapelli, who I saw live many, many years ago. Stephan Grapelli died in 1997. He was a member of the famous Django Rheinhardt Hot Club, an early French jazz band. Rheinhardt had three finger of his left hand (on the fret board) blown off in WWI, yet he was still considered one of the greatest jazz guitarists. Hot Dawg is another of David Grisman's albums I really like. He played "Dawg music."
There is a world of great young jazz singers. When somebody tells me about one, I jot down their name and head for Qobuz. That way I can listen to everything suggested to me. I absolutely do not want to get stuck in the past!
Regarding classical piano, I love Debussy. At times, he is very close to the best jazz. Another piece that I think is wonderful is Schubert's Impomptus. They are absolutely beautiful. If you poke around for it on youtube, I think you can find Mitsuko Uchida. She has the most wonderful touch. I have heard the Impomptus by many pianists, but she is my absolute favorite.