To begin with, it's relatively common these days to see mint original condition low houred late model 4020's with all the bells and whistles bring in excess of $15,000 - $20,000.....
The tractors shown in Machinery Pete's video are NOT "run of the mill" tractors. They're rare tractors because of low initial build numbers (with certain options), which are made even more rare due to the fact that even fewer survived intact. As an example, the 4020 standard, LP gas powered, console model with very low hours....Or a front assist 4020 Powershift in primo condition..... You just don't see them every day. Deere, from the very beginning, has kept detailed records of what they build. (more so than ANY brand) It's relatively easy to document exactly how many tractors were built with certain option, and/or combinations of options. There are a number of options that saw very low build numbers, even in the single digits. In their enthusiasm for collecting, a handful of collectors are willing to shell out big bucks for what may well be now, a "one of a kind tractor".
Also, a few collectors are willing to shell out extra money for "first" or "last" serial numbered tractors. I'm quite sure a few tractors are bought at "money is no object" levels just to complete a series or theme to an individual collection.
These tractors are NOT bought as "daily drivers". So their purchase price isn't generally something that has to "pencil out" as a working farm tractor. The value is set more as a long term investment than as a "what's it worth down on the farm" value. They're bought strictly as collector pieces. As you might imagine, these tractors are bought by folks who have plenty of pesos to spend on items that will just sit in a collection. That puts them in the hands of people who've found the pot o' gold at the end of the rainbow.....People who've got some sense of what (and HOW) it takes to make "big bucks"......People who usually aren't "stupid" with their money. Guys like JD collector Walter Keller. (Who by the way, ended up with a couple of the tractors in the story, as I'm told)
You just don't end up with the money and resources to build a collection like this (see link below) by being foolish with your money.
http://www.antiquefarming.com/PDF/keller.pdf
Now, compound the above with the facts that no brand commands the fierce loyalty of that of John Deere, and that New Generation tractors are now as much as 50 years old (and still a viable working tractor in many cases). It's that old "best resale value" thing, in spades.....
Would I spend 50 large on a 4020? Not likely. Do I understand why someone else might? Most definatly.