Candidates for best speakers in the $2000-5000 market

If I were in your position—needing a speaker that is both aesthetically right and that sounds great—I would start by selecting some possibilities among those that will look good in your room, and then choose from there. There are many choices. 
 

Twice, I was in the position of wanting to choose something that both sounded good and looked good (or at least appropriate) in my living spaces. In both cases I researched and tried a number of options. These choices likely won’t apply to your situation.  In a medium-size room I chose the KEF LS60s, which are proving to be a perfect visual and sonic choice for our living situation. The second choice might be controversial, but for our large room we eventually chose the Magnepan 1.7i with the light-colored, natural grill cloth. While the panels are large, the light shade and ability to move them easily if necessary makes the size almost a non-issue. I haven’t had to move them out of the way yet, and they’ve been in use for 8 years. 
 

Enjoy making your choice!

Four of my friends own Legacy Signature III speakers.  Available at $2000 or under.  Sure they are used.  They beat out every speaker mentioned in terms of dynamics, deep bass, ease to drive (except Harbeths), besides not losing anything of great significance to any of the others.  However, they are moderately large size and weight 135 lbs.  I have them in my second system (paid $1600).   What a bargain!!!  I'm looking for another pair for my TV audio room.

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.