Speakers 10 years old or older that can compete with todays best,

@mikelavigne 

The purist and the early adapter. Black and white. 

My room is also epic and I use dipole linear arrays which limit room interaction, ESLs with an order of magnitude less distortion than any dynamic driver.

I digitize my turntable and use digital RIAA correction which is more accurate than any analog circuit. 

I would never buy another tape machine (I am being given an old Nagra for display purposes only) IMHO they all belong in museums next to Edison's cylinder machines. Recording in 24/192 is more accurate with less distortion not to mention that it is far less expensive, no tape and the software is far less expensive. The only reasons I play records is because I have thousands of them and I've been doing it since I was 4 years old.

Black and White. Two entirely different approaches to the same problem, the romantic and the modern. Both are valid for differing reasons. 

It seems DCM Time Windows get the nod for the most commonly appreciated old loudspeaker

Still loving my Reference 2A MM de Capos

That's an easy one...

My Magnepan 20.1's about 25ys old

My Acoustat Spectra 33's which are about 34 yrs old.

There are a lot of older speakers that can compete with many new speakers today.

Within their obvious limits, a pair of Quad 57s can run with many of the best (I use original Martin Logan CLS and they are fantastic for non bass heavy material).

I also have some  Vandersteen 4A that were at the time his top speakers, made in quite small numbers - all the money went into the drivers rather than 'wasting' it on fine veneers - he just 'put a sock on it' for looks   (Anyone looking at these be sure to buy 4A, not 4).

And the speakers I use in my main system (Wilson Maxx2) still handily compete with many today - and they don't give small children nightmares like the stupendously priced current top of the line Wilsons.