So much depends on the owner and what level of mechanical work and weather exposure he finds comfortable within that budget.
My guess is that with so much acreage and a steep driveway he already knows his tractor is not going to be "push button everything and climate controlled". There will be some old cloths an muscle work involved.
Like Lou says, he can save a bundle with 2wd + chains for winter instead of buying a new part time 4wd. There are no full time 4wd tractors in his price range.
Good news is that all tractors have a locking differential and individual wheel brakes.
My experience is that those two features plus chains have better traction and control than a 4wd without chains - particularly on slopes.
I agree! Both diff locks and rear wheel brakes are super useful in low traction situations.
Please do get power steering,
Especially if you get a loader, which you really should.
He can & should look at the used market. There 2wd is more common. Buying used can fetch a larger popular premium brand of tractor that holds its value for the same money as paying for new tractor in a less well known brand. Only the OP knows what it would take to make him comfortable buying used. But it is always worth considering.
Most new tractors are still available with the optional shuttle/glide/power shift. Those are called "clutchless powershifts" and are very reliable and powerful. Some folks prefer them. They same thousands over a hydrostatic (HST) transmission
Be really careful about what kind of shuttle a tractor has got.
"Shuttle" at a minimum is a separate forward/reverse gear box. Instead of shifting the main transmission into reverse as you do in a car, you use a lever that's usually on the steering column.
The problem is that some cheaper tractors, usually in the smaller HP range, have just the shuttle gearbox. You still have to clutch to go between forward and reverse, and you have to stop to shift gears in the main transmission because it's not synchromesh.
Even cheaper tractors don't have the shuttle, and have non sychro transmissions. You have to stop to shift the main transmission or to go into reverse. Most compact tractors with gear transmissions are like this. Not even a shuttle.
Synchro shuttles have synchromesh in the main transmission and shuttle, so you can change gears while moving, still using the clutch. This is really useful.
Then there are power shuttles where the automotive style dry clutch is replaced by a wet clutch that is hydraulically operated. With these you can move the shuttle lever and it will clutch for you. These are generally found in larger tractors sold for ag use, roughly 65 hp and hp.
There are weird hybrids like my Deere's synchro reverser which is a basic non synchro everything gear transmission except there are synchros between forward low range and reverse range. You still have to clutch between them but the tractor can be rolling.
To keep a set PTO speed you need to run the engine at a certain RPM.
With HST the tractor ground speed is infinitely variable from zero to whatever the max is in the selected range and independent of engine speed. With any of the geared transmissions, ground speed in a given gear is determined by engine speed.
So for example if you're mowing a plot that is on a slope and you want to be in a lower gear for the uphill (power) and downhill (engine braking) legs while going across the slope you can go faster. With HST you just change the pedal position. With a geared tractor you will need to downshift when you start the uphill or downhill leg. If it's a non synchro gear transmission, you have to clutch and stop to do it. If it's got synchro on the main transmission you can shift while moving. If it's a power shuttle you still need to declutch but that may be a button on the shifter.
With any geared tractor, you're stuck going the speed that the gears give you at the engine speed you need to run the PTO. Often there's only the choice between too fast and not as fast as you could go. Some implements don't need exact PTO speed so you can vary that some to get the ground speed you want, depending on conditions.
Of course when you're doing something that does not involve a PTO implement that needs to be at a certain RPM, you can set the ground speed with a combination of gear selection and engine speed.