When I was looking last year, I started by looking for used tractors, but had trouble finding one close enough, new enough, with the features I wanted, for any reasonable price. I finally decided that I had exactly one time at my age to buy one, so get one with the features I wanted, with a warranty. For me, that meant cab with heat and air, HST, loader, and at least two rear remotes. Then I needed to decide what size. For my 12 acres of current hay field, several people I trust recommended a 6' brush hog, which translates to roughly 30 PTO HP as a minimum. With the cab, I went up some due to the air conditioning draw, and bought a Kioti DK45SE with 36 PTO HP. The DK45SE is slightly larger than James' DK35SE, which he kindly let me try out a bit last year. I think for my 12 acres I have made the right decision.
Definitely, decide on the size of your implemnts first, and let that dictate the power you need. Then, go to your dealers (won't say local in your case!) and sit on each of the tractors in the power range you need. Each will fit you differently, and the placement and operation of the controls, as well as your comfort, are important. Some tractors will fit you better than others. Try out the ones that fit you best, and make your short list of those you really want. And do check out the dealership - they will be the ones to make or break your tractoring experience when you need implemets, parts, service, and especially any warranty work.
Once you've refined the short list, it is time to start getting quotes. My short list included Massey Ferguson, Kubota, and Kioti. The final factor in my case was the price, as mine came with a free loader and was several thousand less than the other two.
Most of all, have fun looking! And good luck with your decision.