At a given price point, better to go late vintage or modern?

So to my ears, you are really picking among two very different schools of thought
…

They are both designed as time and phase correct,
They are more similar than dissimilar (IMO).

So one should be able to DSP there way to taste, or the room’s brightness may play a role.

Holmz, I agree.  Not two different schools of thought but different designer sound signatures.  That is, at least with my limited experience.  The Vandy's I have the most time with were 2's, not sure what generation.  They were definitely sort of bland, could listen to those for hours without fatigue.  Sort of had their own loudness compensation to my ears.  

My only time  with Thiels was mid 80's when two friends were deciding whether the Thiel's were up to the task against the original large Advents.  I was partial to the Advents as my later college years had stacked Advents in the house.  Still miss those...

The Thiel's were in your face when pushed.  No clear winner that night except when playing Floyd where the Advents, to my biased ear, better conveyed their concert presence.  

Tomic:

Yes sir, Shure cartridge, Grace arm, Thorens turntable, Apt Holman preamp (still my favorite), DH500 Hafler and the AR9's since the late 80's.

Thanks for the link, one solo listening chair, who's the boss?

AT ANY GIVEN PRICE POINT, the decision varies by individual piece of equipment.  Some equipment was overpriced and not a value even at half price.  Other equipment is a great value even at twice its retail price.  

Only YOUR ears can make the call.

Indeed.

The original question was to seek consensus, generally, if say $6,000 speakers that have now devalued to $2,000 would be superior to younger models at the same $2,000 price of admission.

This whole thought has its origin in my H.T. front 2019 Pioneer FS52 mini towers which for pocket change are more than remarkable, actually stunning.