I can't say I've had any problems with the brakes. And I have some hilly trails I go on, but I let the engine do the braking and don't get in a hurry.
I will say there is some travel in the pedal (1.5-2.0) that I wouldn't think a new tractor should have, but mine will lock the back tries up easily..
I was asking if the tractor you are looking at has the 12/12 transmission in it? I don't believe I would get a shuttle shift transmission, I was told they are the tractors that have had most of the problems, this came from a guy that worked at my local dealer for several years.
We have two new Hollands at work T155s and they are nice, but the clutch packs have been a real problems with ruff shifting. So much so they will pick the front tires up. And backing up the clutch doesn't allow smooth slipping wile backing into a hole with a batwing. Other than the clutch packs they have been solid performers on some very steep slopes daily. But we do have one in the shop right now with metal in the HYD filter..
The New Holland 75 is probably a good machine too..