For the CUT market, where say we're talking in a $15,000 to $25,000 for a "new" price, for me the breaking point is about $5,000 - $6,000. Of course, all of that is extremely situationally dependent. New, as you mentioned, is more or less a known quantity that in a lot of senses is "easier" to buy and has better peace of mind than buying used or nearly new. So anytime someone compares buying new vs. used, it really depends alot on what the used tractor is - hours, conditions, past history, how much do you believe what the seller is telling you, etc.
The only reason I say all of this is because I just went through this decision. At first I was looking for a larger tractor than I currently have, then decided to go for one a little smaller than what I have, and ended up with one about the same size as I have now. I priced new tractors in the same size that I eventually found a used one, and it was about a $10,000 difference with what I ended up buying. However, in the course of the search, as I looked at different tractors, that $5,000-$6,000 range of difference seemed to be what made a used tractor more attractive than a new one, and the greater that number got, the more attractive used tractors looked.
Obviously, the used tractor I bought comes with more risk than a new one, but for the difference that I saved, I can do a lot of repairs, and in my situation, it is a 2nd tractor, so I can afford some downtime.
Anyway, that's my thought, for new vs. used. For new vs. almost new, if the difference is only a couple thousand, I would probably go new....
Good luck and take care.
:laughing: