How does one weigh the virtues an older amp vs. a younger one?

Think of an old car with few miles vs a lot of miles. No comparison. Amps are similar, if you can get an old amp that wasn’t used a lot vs was played hard, it makes a difference. I like my Carver 505 that was built in the nineties a lot and I would put it up against any of todays amps up to $1500.

OP, since you are talking integrated amps, how about a Mark Levinson No. 383.  George Meyer in Los Angeles, who is an authorized Mark Levinson repair facility has completely refurbished units at $3,000 dollars and another for $3,200 dollars.  These are outstanding integrated amps.  Here is the info:

Better to listen to each for extended periods (weeks even), then decide which one you prefer to live with.   You miss a lot of the little stuff doing quick A/B listening.

Yes, truths reveal themselves -or are built into clarity, in our minds- over time.

Audio is no exception.

A saying that goes in that direction, is that we know all we need to know about a person we meet, in the first few minutes, but it takes 30 years of interactions for that to be clear in our minds.

Human interactions with the world, in all their myriad ways, are, of course, some variant of that. No matter how much the ego wants it to be different.

Trying to tie product quality and value to you to market prices is a very bad place to be. You are essentially trying to build up your stereo based on perceived fiscal value instead of pleasure you personally derive from it. Unless you are running a used gear store I think this approach won’t help you enjoy music very much.

Consider that a brand name can make a difference in selling price from 2x on upwards but that’s no guarantee you would like it 2x better. You might also fall in love with something older, or less expensive. Will you buy the less expensive gear you like more?