Best Class A Amp under $2,000 used?

Something closer to a Pareto curve.  Its a surface, not a point.  Amplifiers are systems-of-systems.  Transformer technology has evolved.  Discrete components are no longer +/- 5%.  Some are now chip-ed assemblies rather than PC boards. And line widths are under 10 nm with the upper end of 80 nm dissipating from stocks.  Speakers have changed. Test equipment has evolved.  Recording and mixing technology changed (evolved, arguably).  You have devices now that clock in nano (soon to femto) and a few 10s of milliseconds vs micro and hundreds of milliseconds. RIAA curve has evolved. FCC and CISPR measures and isolation have changed. There are some who find comfort in what they once knew. Economic market value isn't just set by taxonomy- alone or in large part.  Authenticity is now argued with newer, non-deterministic math. Still, some cling to subjectives in prose and poetry to evoke a consensus. Market valuations are just a sum of demand against a supply.  Baby boomers will still prefer a signature sound they have trained themselves listen for. Greenspan's 'irrational exuberance'.   

I guess he is saying we like a certain sound or sonic we came to appreciate when we were younger and still want it despite advances in technology.  It is true, we like what we like and want that, as do many in our age group (boomers)  or cohort, which creates the demand against which supply or build costs, leads to the prices we are willing to pay.

Yes.  I have seen a couple of discussions on the forum about that subject.  A good point. I could see how certain sounds can bring you to memories of how things should sound vs how they actually sound.  As I wasn't privy to owning very good sound systems as a teenager or young adult, I might not be as inherently partial to legacy equipment.  Maybe I would be better off getting hooked on the new technology if it is superior based on the latest testing equipment.  Does anyone care to recommend which amp companies are on the cutting edge of newer technology with in reasonable budgets?  (Whether you like it or not)

you wont get 250w classA anywhere. push a bit your budget if possible and get the Benchmark AHB2.  It plays well above its price and is a near perfect audio tool. You will have everything you will need amp wise for the next 15 years.

Average listening uses only a few watts.   I recommend a single end triode (SET) amp using 211 or 845 output tubes for 12 to 15 watts of pure class A power.        By the way, you did not list your speakers. Amplifier/speaker matching is important! Same for your signal source: analog or digital?