I farm for a living, so I look at things a little differently.
You didnt give a dollar amount but assuming you've got a good sized budget, personally I would get a good sized (75+ish hp) tracked skid loader with high flow hydraulics, a/c and heat, then get a late 60s or 70s vintage tractor, something maybe 60-75hp, something with wide front, power steering, and a 3pt. Color doesnt really matter on that vintage, so if you have a preferable brand that's fine, tons of parts available from the aftermarket so you dont need to be reliant on a dealer. One tractor I'm familiar with would be a 1650 or 1655 Oliver, they were a midsized tractor in their day so they werent worked as hard as the bigger ones. Lots of them had loaders too. Itd be big enough to pull a 12-15ft disk, a smaller plow, 10-12ft no till drill, 4-6 row planter, can Bush hog if you want, basically it's a good all around size. Plus they're dead simple, most things can be fixed with basic hand tools.
The reason I say go this way, is from what I've run and seen, most modern tractors dont hold a candle to their older sized equivalents. A 75hp tractor today will get spanked by one from the 70s when it comes to doing real work, plus they dont even make decent loader tractors IMO. We borrow a guys 100hp modern tractor, it needs the FWA to pull a 12ft disk where something like a 1650 will pull it fine in 2wd. Plus the older tractors are WAY more stable.
A good sized skid loader like I mentioned will do a hell of alot more work than a loader tractor. Plus the never ending plethora of attachments you can rent or buy is mind boggling. Tree mulchers, tillers, dozer blades, the list goes on, plus you can load it on a trailer and haul it wherever. If you need a tiller every year, might as well rent one for the weekend instead of buying.
Just my $.02
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