The longer I swim in this swirling vortex passion the more I know the room is key. Some or a lot of room treatments can not be ignored. Power too.
The room daddy oh; the room will make it copacetic (said like Ben Sidran or Ken Nordine).
For me Jazz is better on Analog systems unless the system is high ($$$$) end.
I happy listen as you do (now playing Wes Montgomery D natural blues) using a PrmaLuna HP (KT120's) and Sonus faber Guarneri evolution speakers (now easy to find at 1/2 to 1/3 of their original price same for PL integrated).
Any and all of the above are great recommendations. A great speaker and systems will do justice to all music excepting gamelan music. That's not my cup of tea.