First off, I think you need to have a clear idea of what you want to do with the tractor so you know how many horsepower it needs to be and what kind of 'features' it has to have such as external hydraulics, pto, or a three-point hitch. What size of a mower do you want to use? Will you want a front end loader, or front end attachments. Will you need to have external hydraulic controls, if so, how many? If you want a three-point hitch, will it need to be able to push down as well as lift up? If you want to carry round-bales, how much do they weigh, you will need enough power to pick them up. Is there any chance you will want to ever run a swather/cutter or baler, if so, you will need to know how many horse power that will take. What kind of tires do you want on it? There are you standard 'farm' tractor tires with deep v-shaped type of tread, turf type tires that remind me more of a car tire, and an inbetween type that is a less aggressive v-type of pattern. Do you want a diesel or a gasoline engine?
Once you know the horsepower needs, and which features you want, then you can compare prices. There aer some well known brands that have excellent reputations, and there are some lesser known brands that are also very good. Then there are some cheap imports that don't have a lot of quality. Having a good dealer to work with you through the years will also be a consideration.
My husband originally had an old 'gray' Ford tractor, even though it is one from the1950's, there are still a lot of them in use today. It did nearly everything we needed, but it couldn't pick up the big bales of hay. So, eventualy he decided to get a bigger tractor. We bought a 45 horsepower, front-wheel assist, diesel Kioti, which looks almost exactly like a Kubota. We also got the front end loader and a front round bale 'squeezer', and of course the three point hitch and PTO. Our three-point is only 'power' going 'up', and gravity going down, and there are occasions (like when trying to dig fence holes) that we wish it had power to push down. However, we love that tractor and have had it about five years now, and believe the Kioti is a very well built tractor. However, now he is kind of thinking that maybe he should have bought one with even a little more horsepower. Last year he bought some 'small' haying equipment, a 6' disc mower and a 'small' round bale baler. Although the 45 hp is working, it is struggling with making full, tight bales. So, now he wishes he had opted for slightly more horsepower. Going up in horsepower from the 45 to the 65 would actually have made very little difference in price. So, if in doubt, I would suggest you getting a larger horsepower than you expect to need. Of course, on the flip side, my husband would not consider getting rid of his original 'gray' Ford tractor, as there are some jobs that are so much handier to do with the smaller, more nimble littel two-wheel drive tractor.