As some have said, a great player will make an average guitar sound good, but it's like asking Mario Andretti to drive a Yugo in a race. Even a pair of $5000 guitars from the same luthier may sound different, as each piece of wood is unique. Well aged and often played guitars also change in timbre over time, and generally for the better. A well recorded classical or steel string guitar is a joy to listen to on a fine system.
Can you tell the difference between a $200 and a $200,000 guitar?
Can you tell the difference between a $200, $2,000, $20,000, and $200,000 classical guitar? Direct comparison starts at 27:39.