Unfortunately the boomer generation is starting to fade as with it the demand for even some of the rarest pieces. We see that now with Standard Guage in that the generation that would collect that is passing on.
True. But then there are those of us who would buy if the prices weren't as high as they are.
The disposable income factor of a specified generation does help skew the supply and demand curve to an unnatural high. Especially if you add the "one-ups-manship" variable into the equation. Those who have the means are often willing to pay prices higher than the market could or would normally produce simply to have something better than what "you" have. The equalizer to everything is the demise of the inflationary element. When that occurs, the prices should return to a level that's more reasonable for the specific market to handle.
It's the initial owner/seller who sold the item to the buyer with the big wallet that stands to have the greatest monetary gain. Typically when that high priced buyer passes on, his or her family sells the item far below the initial investment cost. Often because they have no idea what they have. We've all see it, it happens all the time.
Bottom line, buy what you like because you can use it for your specified purpose during your lifetime because your heirs may sell it for pennies when you're gone. Personally I don't have 500 bucks to spend on a 385E. But that doesn't mean I don't want one.