I'm going to just jump in here with my perspective as a younger guy (32).
I own and am fixing up as Massey 230 as I use it. I need it to keep 5 acres of pasture mowed and ~300' of laneway free of snow.
I'm looking for a second tractor as the Massey is going to need a fairly substantial overhaul (well, replace the electrical harness, lighting and instruments, replace the rad hoses and and fuel tank mounts) in the spring and given my limited availability, it probably means it will be a several week or more process during which the tractor will be 'down'.
While I have the room, I have no interest in acquiring a private museum of tractors that have little utility to me. For me and a lot of guys, tractors from pre-1950 (or even pre-1960) seem to have little practical use other than as show pieces due to either low power or lack of attachments.
To go even a step further, out here, 3PH is predominant and you can't find implements for Fasthitch, Eagle Claw etc... A tractor without 3PH is also viewed as 'worthless'. (Yes, I know Eagle Claw can be made to work with 3PH implements, but most guys don't want the bother).
Finally, the market out here for older tractors is a bit pathetic - your examples are either rusty piles that have been in a fenceline for decades (and still $1000-$2500), or $8-15k barn queens that they are trying to get every dollar of their restoration costs back out of *and* get paid for their time.
The best value is in the 60's-70's-80's tractors that you can pick for $4k-8k right now.
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