Bought new (Kubota 2601 + FEL + belly mower + rotary cutter) because a) I can depreciate it, b) I got 0% financing with zero down, c) because I really don't know a heck of a lot about tractors (but learning fast) and am not qualified to assess good one vs. bad one, d) I needed it to go to work NOW, not after I learned to fix whatever might have been wrong with a used one, e) warranty!!!!, f) I didn't want to get sidetracked into another "project" - I have enough of them right now.
To be honest, I bought a tractor not because I wanted a tractor, but because I needed some land cleared, then mowed, then pallets unloaded, etc. etc. The tractor is a tool, the fact that I enjoy using it is a side benefit. It has paid for itself a dozen times over, and that is just so far. There are times when having your own tractor is like finding a thousand dollars in your wallet that you didn't know about.
It is like a camera - nobody buys a camera because they want a camera, they only buy a camera because they want photographs.
YMMV.
Best regards,
Mike/Florida