DL,
Waiting for the tractor to "tell you when" you need to be in 4wd may work if you are always on flat land. But if you are in areas with hills, you don't have the luxury of waiting for the tractor to communicate to you. Jeep experience won't help you in hilly areas if you are going down hill on a tractor because your Jeep had 4 wheels of braking and many tractors only have 2 wheels of braking. In addition, Jeep experience doesn't include outrigger issues that tractors do, like front end loaders.
Driving a hydrostatic equipped transmission tractor of any size in hilly areas is far more complicated than a jeep or motorcycle or atv. . . . Far more.
All tractors I've seen have brakes on their rear wheels but I've not seen tractors that have brakes on their front wheels. . . Have you ?
If you are going down a hill in 2wd and your rear wheels get "light" . . . You are out of control and at the mercy of gravity. If you have a fel on at the time it will either increase the pull of gravity, or create a "pole vault" potential for a flip, or if the hill is gradual enough. . . Give you a risky chance to slow yourself.
In 2wd in a hydrostatic system you have no no no engine braking if the rear wheels get "light".