Welcome Blackgreyhounds!
Exciting time for you. I'll add my 2 cents to the great feedback above. In my opinion the dealer, (both sales and service experience), should be a big part of your decision. After a very similar recent process looking for a new tractor, we decided on the Mahindra 2538 for our 17 partially wooded acres. We had a Max 25 that was great on 2 acres and bullet proof, but needed more capacity for this tract. So far I am very pleased with this heavy mid sized machine. The Kioti, Kubota, Branson and JD comparables all were reviewed and some tested as well. All very nice and comparable tractors. For me personally the Mahindra was the most bang for the buck and had all the features I needed save for Cruise and a Suspension seat, so I ordered those and they were installed before pick up. It is not a Cadillac, but it IS a tractor, so there is that...
A few factors that I found personally important were a beefy front end and tires for lots of loader work, good lift capacity, sufficient built in weight, a tier 4 final engine with NO DPF or DEF, and the five year powertrain warranty. (Among other things...)
Whatever brand you end up with, I would recommend a grapple with third function kit. Really makes working with brush and trees so much more pleasant. That is what I mainly use mine for along with cutting using a 6' cutter, and moving some dirt with 6' box blade. The tractor handles these implements with ease. Another nice thing is that it is big enough to get things done, but still sized to work well in slightly tighter areas. It's not a 50HP utility tractor, but pretends to be from time to time.
You'll also find good threads on the 2538 over at the Mahindra specific forum where others have shared additional thoughts a well. Most all reputable brands are good, and all have their minor pros and cons. I think you will be happy with any color tractor assuming you get into the right size/weight/capacity range you need. Good luck with your decision.
As for possible hauling - the 2538 with a 6' cutter, 6' box blade, grapple and original bucket all fit on a 20' trailer, and can still be hauled by a half ton, but just barely...