I wouldn’t necessarily call this an exercise. For me I look at impact (across genres even), quality of catalog (studio and live performances + bootlegs even) as well as originality. For me I can’t go by how the music makes me feel. With most of the greats, I can say that a majority of their music hits the right spot.
Now to speak on your main 5 go-to guys (if I can call it that).
Dollar Brand is definitely one of the greatest pianists (top 5 even… lol). He definitely has excellent stuff.
Miles… I will always have a love/hate relationship with his catalog. I love pretty much everything until Bitches Brew, after that not too much more. I know Miles is at the top on a lot of lists. I think that a lot of stuff wasn’t good from the 70’s through the 90’s. I think his sound changed drastically when Tony Williams left. When Miles tried to do what Lifetime and Mahavishnu was doing, it didn’t sound as good. Still has a good enough body of work where most folks would have him near the top.
McCoy… did legendary work with Coltrane and had several great recordings of his own. I like the other two pianists that you mentioned better though.
Shepp… definitely one of my favorite sax players. You can’t go wrong with anything in his catalog. I even messed with that Ocean Bridges with Raw Poetic and Damu. Definitely should get mentioned more as one of the greatest musicians.
Jarrett… could be top 5 in my list and was until I moved Don Cherry in there lol. There is really so much that you can say about him as a musician.
I know that over time our feelings change. As for me, Cherry and Ayler grew on me more and definitely had great impact on the genre. Ayler died young, but his sound is definitely undeniable. Probably I would have to put him as the best sax player that I’ve heard. The others have always been in my tops list.