New Speakers under consideration - but I’m afraid

I’ve been able to compare Joseph Audio speakers to B&W over the years and found the JA speakers to be superior in every way.  They disappear better, throw off a more expanded and believable 3D soundstage, and they provide all the detail of the B&Ws but just do it in a more “natural” way is best I can describe it.  This is to say if you can demo JA speakers I think it would be very worthwhile.  For reference I compared the JA RM25si to the 803N back in the day and more recently the original Pulsar to the 805 D3.  Best of luck.  

I think you can definitely improve on your old B&Ws. But let's appreciate that they gave you decades worth of enjoyment! Best bet is to find a good semi-local dealer and see if you can listen to some options for yourself. Then see if you can try the ones you like best in your own home for a while. 

Volti Rival, these are speakers done right 18k or less, not sure

DeVore O96, Fleetwood, made in new york $15000

Joseph Audio, Perlisen 

Klipsch

Sonus Faber, these are very good with Mac

I have looked around in Chicago and several of these as well as other good brands. I have not heard all the above so some are opinions of others.

Yes I understand your concerns which are all very valid, but changing speakers is always a challenge and more so if a home demonstration is not possible.

But, nothing venture nothing gain.

Audio shows have their limitations in assessing different speakers for all sorts of well known reasons. Finding ones that have the right synergy with your existing system is also a key consideration.

I am on my third pair of YG speakers, namely Hailey Reference 2.2 , which I consider to be outstanding but well above your price range. A used pair of Carmels could be an option if you like their sound.

I was attracted to YG by a review of the Carmel 1s a long time ago  and I paid my first visit to Munich specifically to hear them. The room YG had for that show was excellent and their sound confirmed what I had read.

In my experience audio components all have  distinct characteristics  to their sound and all my three pairs of YGs have reproduced and brought out their differences and nuances because of their inherent and first class neutrality.

Going to one of the shows mentioned should give you an opportunity to assess different options and find some that appeal to you. Careful reading of review, ie reading between the lines, can often provide the additional insights to supplement your show listening experiences.

In my experience it is a journey worth making as long as you do your homework and take your time. It is one that can bring significant rewards

If I were in your shoes, I would be looking at pre-owned (5-10 years old). You can still make a big jump with technology and get a great used speaker in the $15-$25k range that once retailed for $40-$50k. Magico, Focal, Rockport, YG, etc. Take your time, read the forums and reviews.