To misquote Dr. Seuss, "Oh the fun you'll have". You will get lots of good perspectives on this thread. I would start by going to dealerships and just start looking around. Sitting in the seat and driving around the lot will give you some idea what you like and what you don't like as far as size and features. It will also give you an idea if each dealership and/or salesperson is willing to invest time with you and talk straight, or if you are just a cash transaction to them. Warning, this will also get you in a spirited mood to buy!
I grew up on a farm with John Deeres from the 50's and 60's (gas and diesel). Off to college and career, and then a country home with a 1/2 mile driveway. A Farrmall H and a pony grader took care of that. The farm got select cut, and now there were 160 acres of trails to build and maintain. Hard to justify big bucks to the better half, so started on a budget - a grey market 15 hp Shibaura 1500SD AO with a 4' Kingkutter rough cut mower ($2,900). Amazed at how tough that tractor was - mowed hazelnut brush 8' high, and it barely sipped the fuel. Came across a 24hp John Deer 850 with a loader and 5' rough cutter for $6,000, so sold the Shibaura for what I paid for it even after years of use (love how compact utility tractors hold their value). Used that on the farm trails for years, and just sold it for $1,000 more than I paid for it and kept the rotary cutter.
By now, I caught the compact tractor bug. I bought a 21hp New Holland TC21 hydro with mid mount mower and loader to mo my mother's yard (farm), and I came across a 33hp New Holland hydro with loader for my own place. These newer compact tractors are amazing - smooth hydraulics, power steering, open platforms, smooth running diesels, etc. I thought I had my perfect tractor until ...... the BIG, HEAVY, WET snowstorm hit. I got it done with the 33hp New Holland with loader and rear mount snowblower, but a lot of tire spinning with the R4s and the deep snow.
A friend of mine wanted my tractor, and I found a 40hp New Holland 12x12 shuttle with loader and R1 ag tires. I have now found my perfect tractor (until the next one). Only 7 more hp, but the larger frame and tires mean everything as far as brute force. Night and day difference as far as what I can do with this tractor, and yet it is nearly as nimble as my 33 hp version. A long story to get to my thoughts on your tractor considerations:
40 - 55 hp larger frame tractor
Hydro or Shuttle? I like em both
Pre Tier IV engine (too many uncertainties for this large of an investment)
Extra hydraulic remotes (for grapple bucket, top & tilt, rear implements, etc.)
Extendable 3 point links (I no longer consider this a luxury)
A good dealer for parts and service
John Deere, Kioti, Kubota, Mahindra, Massey Ferguson, or New Holland (in alphabetical order)
Beet juice in the tires
I sure like my R1 ag tires, but R4s would be okay too. Add some LED work lights, a tool box and chain carrier and you will be good to go. Recognize that you are about to begin journey that others may not understand ...