Hey Joe Praha,
Welcome to TBN. Keep coming back.
I've been tractoring for over 50 years. Big isn't necessary anymore -- except to impress the neighbors. But, I wouldn't even think about buying a tractor without 4WD, unless it was to cut a 1/4 acre lawn.
The Mahindras are heavy. If you have the tires filled, the tractors have even more traction. Couple that with 4WD, and it is amazing what they will do. They'll move a lot of dirt and snow -- without chains. With chains, you can probably damage FELs and blades if you aren't careful. They are well designed and incredibly tough tractors. Backhoes are available for all of the 15-Series, which you can move with an F150.
With a box blade, brush hog, and Front End Loader (FEL) you can do a lot of landscaping.
I love my Mahindra. But, most of today's top name-tractors are all extremely good. Kubota, New Holland, Massey, John Deere -- it is hard to make a serious mistake. Good dealers and good support are what make a good tractor.
Each brand has their own great areas, and their own minor weaknesses. Actually, I haven't found any weaknesses with the Mahindras -- great tractor, great parts support, great support on this website through Mahindra USA, great support on this website through Mahindra owners, and, at least for me, a great local dealer.
But, if you think your tractor wants to be a Yooper, don't even think about 2WD from October to May. Over 200 inches of snow per season, -50 degrees F, ... well . . .
How about mosquito control? I think I'd consider a cab. Cabs are available for most of the Mahindras.
If you are going to use a tractor up there, I wouldn't consider buying it down south -- the trolls below the bridge don't know about cold and snow. I'd talk to the boys on the U.P. about tractors. They'll know about fluids, heaters, transmissions, tires, etc. My little Japanese diesels might grump about the cold and snow here in the hills of WV, but I don't think they'd even think about coming out of hibernation in a Yooper winter.
Also, if you get the tires filled, make sure you get them done on the UP where they will be filled with something that will withstand the cold.
Good luck. Let us know what you decide.
A Northwoods refuge,
Knute