In regards to my primary question, I decided the answer must be "yes". There are DACs that can be had for $2500 or less that are being compared to DACs that cost $7500 in 2005. My CDP was considered Class A by Stereophile back in 1998, and I think the retail for the whole thing was $3000 when it was released.
I read intently about the Aurilic Vega and the Schiit Yggy. I don't have USB, so the Ayre QB-9DSD was out of the running. I came away with the conclusion that all of these are bested by the MSB Analog in a small amount by almost every measure, but that they are the cream of the crop in the $2300 to $3500 range. I could buy the new Schiit or a used Vega for about the same price.
I decided to take the plunge with Schiit. The reviews pretty much put the two DACs up to individual preference, but it was the company, their history, philosophy, and warranty that swayed me. Also, the 15 day trial makes this a low risk purchase.
I like the 508.24 but I couldn't get over the fact that I must be missing something. I think it was about 10 years ago that I listened to a top-flight setup driving Wilson Maxx2 speakers. They played my copy of Dutch Gramophone 1812 Overture, and the choral sections were phenomenal. I've upgraded everything else in my chain, and I still don't hear the separation of voices in my system. I'm not fool enough to expect Maxx2 dynamics or soundstaging with Revel Performa 3 M106 speakers, but I think they are capable of much more detail than I'm hearing.
I'm excited! I'm hoping for a big bump up in resolution, dynamics, and soundstage.