Candidates for best speakers in the $2000-5000 market

I purchased a used pair of Vandersteen 5As for $6500.  At that price, very hard to beat plus as you upgrade your equipment, they will reward you with better sound.

I was on the same quest as you a few years back - my budget was < $5k a the time which lines up nicely with yours now. I was hoping to - for the 1st time ever - build an affordable high-end system from used high-end but still sounding good gear. 

What I found is that when you're talking about "affordable high-end" you really do have 2 different products: the affordable side of high-end (Sonus faber, Vandersteen, Von Schweikert, Revel...) or the high-end side of affordable (B&W, Paradigm, PSB, Canton ...). Typically the affordable makers are better at containing costs and the high-enders are better at well, that. I explored both with an open mind but expected the former to win out. 

I listen to a little bit of everything from classical to uplifting trance. I demand a loud and dark midrange that dominates an immersive sound stage. I want nothing but punchy, powerful, tight accurate bass with no bloat and no reflections as well as rapid decay. Give me balanced highs with proper weight that are not loud nor overdone.

I drew in my mind the speaker that would fit my sound: a tall thin rounded-back cabinet, no rear ports, large midrange with low crossover points, dome tweeters, small powerful woofers - 2 - not 3 - and not large - light and punchy. I used that image in my head to search for my speakers but kept an open mind. 

I fell in love with the sound of Dave Wilson's speakers but I cannot afford those although used Watt Puppy's sell for the top of your range. I was never able to find and listen to the Von Schweikert VR-4 JR nor the Dynaudio. I did listen to many and I found these speakers to stand out: the Revel Performa line, the Sonus faber Venere and the PSB Imagine (they were only $4k back then). The B&W CM series bass was too heavy for my listening room. 

I settled on the Sonus faber Venere 3.0 + the center for $3k brand new. I paired them with Krell Evolution series gear (S-1200U / Showcase 5 amp - balanced - $2600 for both used - sent to Krell and topped off). The sound is unimaginably  good for what I paid: warm but lively - I feel the drums as much as I hear them but not in a harsh way. I feel like i'm sitting in the bar / concert listening to the band in front of me. 

I did have to use the parametric EQ in the S1200-U to get the speakers to sound how I wanted them: I boosted the midrange and cut the highs (those tweeters are really loud). 

Start with Sonus faber, Revel and probably Canton and go from there. But try to imagine what speaker you're looking for up front. 

Good luck!

Thanks you for so much feedback.

I was close to dealing for a pair of Harbeth M30.2, but had second thoughts after finding ASR’s reservations. They would likely have been a short term experience pending release of the LSA 100 Statement in January, with the intention of ordering a pair of Sonus Faber Electa Amator lll later that month.

This week I added a used REL T/9i to my system, adding the SVS SB-3000 Pro to the 7.1 system in the family room. The "new" sub seems like a breath of fresh air for the Dynaudio Special Forty’s.

So many good speakers, so little money, room, or time to own them all. I’ll vote for what I own: Vandersteen 2CE Signature IIIs, a true classic and great buy. Your spousal unit may not like the looks with the black sock, and if I replace mine I will likely get the Vandersteen Treo CT, which are gorgeous and pass the WAF (wife acceptance factor). The Treo CT is also listed by AbSound as a bargain and classic. (Of course, if I had a bottomless wallet I would ownw other brands too, in my imaginary 2nd/3rd systems!)

AbSound / 50 Greatest Bargains in High-End Audio

Reading some love here for 3-5 year old second hand, for example, as a category?

Correct!