Yes, I understand the thought experiment, but I am challenging a few of the underlying assumptions you have. Mainly, that $1000 makes sense as a cut off point.
If one is able to spend $1000 dollars, a not insignificant sum, on audio equipment, then several other factors I believe follow.
One, this individual has the ability to save up at least four figures worth of income on a hobby. If four figures savings is possible to spend on this hobby, it necessarily follows that more is possible, given more time.
Two, this individual has enough free time to research, evaluate, and enough committed interest to get the point that they have made the decision to spend four figures on audio equipment. This implies a certain amount of free time, personal freedom, and again, income saving potential.
This leads to the next point, which is a frequent excuse, in that a person lives in some remote isolated location near the arctic circle, and cannot possibly demo or try any equipment, because it is simply not possible as there are no audio stores within 1000 miles.
I will also challenge this assumption, because again, if someone has the wherewithal to save four figures for an audio purchase, has the free time and interest necessary to research and understand the hobby enough to want to commit those funds, and further, lives nowhere near an area that allows them to sample these things yet is prepared to buy them sight unseen based on the aforementioned research - I will posit that this individual also has the means to buy a plane, train, bus ticket to a high profile audiophile event such as a CanJam, and sample copious amounts of such equipment to their heart's content. "It's simply not possible for me to try equipment" is not an excuse in a world where travelling from New York to Beijing costs a couple hundred dollars.
Again, if you are on a budget, and you have four figures of money to spend on this hobby, you owe it to yourself to fully explore your options.