The reason why the price of used equipment has become so inflated is because the CB'rs are involved and they are the type of person that wants every penny that they paid for a radio - 20 years ago, when most electronic equipment depreciates almost 25% per a year - excluding high end stereo equipment.

The previous generation couldn't give away their old rigs and yet when the internet came along, and eBay, all of a sudden that old equipment now demands a premium price.

WHY?

Because eBay is rigged and people are stupid!
There is nothing to keep someone from making sock puppet accounts and bidding on their own equipment and setting the price so high that they get the price they demand or they relist it a week later and it is right back on the web site - for weeks, or months or years until finally someone buys it or they throw it away.

At one time, the sellers all knew each other and they set the price by bidding on each others equipment and then stopping at the price they dictated that they wanted for the item. If you want the item, you are going to pay a premium price or you aren't going to get it.
The honest seller can't make a go of it because no one will bid on their equipment unless they are practically giving it away.
And the unscrupulous seller that says - it worked the last time I tried it and then sells it without the power supply or the microphone, hopes that you buy it and don't hook it up until the dilemma period for returns has expired and then you are stuck with an old boat anchor.

It only stands to reason that 99% of the junk that you see at hamfests is junk. If the radio was any good, it wouldn't be for sale! The same is true for amplifiers and antenna tuners! Most people are thief's and their goal is to rip off someone the same way they got ripped off when they first became hams themselves. And that is the reason why you have a real hard time selling anything to these new hams. I'm sure that a lot of them doesn't trust someone to sell them anything and the ones that does buy something, needs to buy it with a credit card, because they are broke as a joke and can't afford to pay cash for something good!

The question you should be asking yourself Gareth is - why do people have $90 a month for the cable bill, and $100 a month for a cell phone bill and $60 a month for an internet bill and yet they can't come up with $1800.00 to buy a new Kenwood TS 590 so they can be hams?
The reason is because it takes two incomes to make a go of it and in today's world, if the woman is not interested in it, then the man is not allowed to spend his own money buying things to be a real ham!
The woman wears the pants in the family and she dictates what the man can or cannot do! The stuff they want - a nice house, a nice car, vacations, furniture, clothes, kids, going out to eat - they have no problem coming up with the money to pay for it. But when the man wants something for himself he is asked - can't you find something a little cheaper, or can't you do the same thing without a antenna, or can't you give it up so I can have the things that I want or need?

Once the kids are raised and gone and the woman gets old and the guy is tired of screwing her anymore and they have a disposable income, then money is no object and for some people instead of buying something good, they want what they had or wished they had when they were kids - even if what they want is junk! A person will spend an outrageous amount of money on junk if it has some sort of nostalgia or sentimental value!