It is simple unless you make it complicated.
1) Figure out what you "need" for a tractors (specs)
2) Visit all dealers in your area who carry tractors that meet those specs - you are looking to determine 2 things:
a) Which tractors do you like the best (seat of the pants feel, how comfortable it is for you, how logical the operating station for the way you think)
b) Which dealer will support you the best during AND AFTER the sale.
With any luck you'll be down to one choice. If not you've got some good dealers in your area, or two tractors are very close for your personal comfort. Just pick the one you lean towards
I purchased a Deere recently and went to my two closest dealers. I ended up purchasing from the one that was further away due to reputation, how they treated me (no BS), and a good solid price. I'm fairly certain I could have shopped a bit further afield and gotten a "rock bottom" price, but these folks gave me a very, very good price and are known for taking care of their customers extremely well - which is worth far more to me than a few hundred $$.
Besides, looking at tractors can be fun
And you don't need to look at every single brand in the area - after operating a treadle hydro tractor I knew that I personally didn't like them (though I'm sure I could get used to it if other things were "better"), so I focused on cabs with two pedal hydro. Kioti's were nice, and much cheaper, but the fellow who had the dealership lost it and locally I would only have purchased from him. IMhO Kioti really shot themselves in the foot closing lots of small mom and pop dealers. There were some folks that were local and gave great services and really had a clue. Between that and the fit and finish and factory extra options that I wanted (more scv's mostly) I went Deere.