Which speakers should I get. $500-$1000

Don't know what amp you have, but Totem Arros are for sale right now on Agon for $800. A great speaker for it's price; full range with wide, deep imaging. Also look at the Totem Dreamcatcher bookshelf. Same great Totem sound, but you would need a sub.

*(I am not associated with these speakers for sale)

Mirage M5si's. These are GREAT on jazz and classical. They have a fast,
transparent midrange and bass extension down into the mid-20's. They fire both
forward and rearward, energizing the room similar to the dispersion pattern of
live singers and musicians. You can consistently find these in like new condition
for around $700. They were $2K new in the mid-'90s. I bought my pair in 1996
and still listen to them daily.

They scale up and down according to ensemble size very well. Tonal balance is
realistic. Easy to lose yourself in the music. And with good amplification and
cabling, they will maintain soundstage and clarity with big band and large scale
orchestral music. Small group jazz is effortless and natural sounding. Plucked
string bass is particularly realistic sounding.

Monitor Audio RS6 is a very well reviewed speaker that usually sells for around $600 used here on the Gon.
Good luck and keep us posted.

Vienna Bach Grand, Dali Ikon 6, Quad 22L2

Another vote for the Vienna Acoustic Bach Grand. A Primare I31 would be a cost effective amp match.