Old vs New Dacs - Best Bang for buck???

How much better are the newer Dacs compared to the better ones from years ago? Has anyone compared?
I am looking to replace my CD player(Esound - which sounds very good to my trained ears) with a DAC. Looking to stay under $500.
I have read that the older 20 bit DACs like Parasound 1100, Adcom 700, Sonic Frontiers and Assemblage Dacs which sell in the $200+ range compare to some current DACs upwards of $1K.
How would they compare to the current better dac like MF V-dac, PS Audio Link Dac, etc?

The old Counterpoint DAC-10A with the upgraded 20bit ultra-analog card are very good sounding (I had one). They do come up for sale in your price range, but don't usually last long on the market.

I can't think of a $500 DAC I would rather have?

This question comes up about once or twice a month here. I suggest that you search the archives. You will get opinions from both sides of the fence, but your opinion is the only one that really matters (to you anyway).

Check out the MHDT DAC's. Lots of info here about them. I tried some of the other reasonably priced DACs and in my system, the MHDT just sounded more "musical" than any other. I've stuck with it for quite a while and would probably only get rid of the Paradisea+ that I have to upgrade to a Havana someday... Now, if I could just convice them to put the input control switch on the front! :)
Try the TADAC 24/96 tube DAC Vert Sweet analog sounding. One can be had for your price renge on A-gon
MHDT Labs DAC's are the best I have heard in that price range. Actually, they have been some of the best I have heard period.
There have been so many advances in chip design since the early days of digital, that it doesn't make sense to hunt for a vintage DAC, in my opinion.

Can you clarify what kind of sound you're looking for? Detailed? Smooth? The PS Audio Link is more of a detailed sound. I haven't heard the V-dac, but it gets a lot of praise in the budget category. The Paradisea sounds wonderful. Very smooth and natural with plenty of drive and punch. I wouldn't call it detailed, but it's not grossly lacking.

There are so many new DACs out there. It would be great to see someone do a shootout.