9 years ago I was in the same position. I looked at used tractors and I just couldn't find one that I wasn't taking a risk on repairing in the near future. Unless things have changed all of these tractors are made in the far east including John Deere and New Holland (Ford) and of course Kubota.
I also looked at Massey Ferguson but shied away from the Eastern European brands because of the problems with their parts and warranty work. You can find parts for a 75 year old JD, or Ford, but not much else. I bought a Ford (now New Holland) 38 PTO HP Diesel compact 4WD tractor. It is big enough to do a lot of work and small enough for me to pull on a fifth wheel trailer with my truck at about 7,500 lbs. total weight. 4WD allows the tractor to pull implements and do the work of a much larger 2WD tractor because of the additional traction.
I haven't had any problems to speak of in the past nine years and I could now sell my "used" tractor and get a new one without spending too much additional money. I bought a front end loader with the tractor and I have never taken it off. I have a box blade, brush hog, finish mower, offset disk and grain drill that I use for planting food plots and mowing.
I wouldn't hesitate to go with John Deer, Kubota, or New Holland tractors. Dealer location, initial pricing and parts costs would help make the decision easier. Check on the cost of an air filter, oil filter and transmission filter for each brand and see if there is a big difference in price.