The reason they call them "Golden Ears" is because they make you shell out more gold to satisfy them. If you have the misfortune to have an organic variation that makes your ears better and more accurate listening instruments, that is a curse, not a blessing.
I think the $1000 figure is a good guestimate at where the average person will start to see diminishing or non-existent returns for each dollar they spend. But that point is going to change based on an individual's organic predisposition as well as to how much time they have invested "Learning to listen" critically.
Bottom line, I don't think a $99 system will be sonically equal (on average) to a $1000 preamp driving the same setup. IO think that is true even if the $99 system is just used as a PRE/PRO. I migrated to separates slowly, and I could hear a difference between my $200 Kenwood Receiver as a Pre/Pro and the Rotel I bought, and so could others who came to listen.