Over the last 40 years, I've bought quite a few really awful looking tractors that were in generally good mechanical shape. Some basic maintenance, a little paint, maybe a new seat, a new battery (or crank), and probably some new decals -- and I could generally sell them for half-again, to as much as three times what I paid for them. In the mean time, I'd get a couple hundred hours use out of it. Except for an old Allis-Chalmers C, I don't think I ever lost money on one.
But, I just don't have the energy I had 20, 30, and 40 years ago.
I bought my first-ever new tractor last year. What a pleasure to know that I don't have to fix something before I use it.
I took a 3-year loan on the new tractor that will be paid off in less than one year. Between all the work this little tractor has already done, and knowing it will probably outlive me -- I don't care if it pays for itself. It's like a best friend, and you can't put a value on that!