I bought new (but an older model) after being advised that for haying you need the tractor on the day the weather breaks. I wanted diesel for fire and fuel economy reasons.
All my other machinery is old and used. The tractor is the only thing that I've never had to tear into to repair or refurbish.
If you are handy with tools, have the tools, and have the time to straighten out other people's messes, have at it. Buy it for life, though. That means not to small or too big.
My requirements: Live power, 4wd, easy on/off loader, loaded tires, trailerable, successful local dealers around, name brand, fits in the barn, and enough power to run hay equipment.
I made the right decision of a JD 1070 after borrowing a JD 4020, IH 1066, Yanmar 220D, JD 4430. That was about 25 years ago and I've never had a single regret. Added a snow plow, pto generator, 7ft' finish mower, 6' box blade, post hole digger and an 8' landscape rake.
The one surprise is all the things you can do with a loader that are not typical loader bucket functions.