I second what Jon said.
I currently have one 20 year old machine L3450 (1220 hrs) that is GST. I've run newer ones as well, only thing you have to keep in mind with the GST and hills is that when you shift gears on the fly or shuttle from reverse to forward on the fly, there is a slight period of time where the trans is in a neutral state, so, if your on a steep incline the tractor can pickup some speed from gravity. The newer machines seem to have eliminated this sensation, but in either case, once you get used to it, it's not really an issue.
The DT tractor would have to be brought to a stop on that hilly area, which means you'd have to use the brakes anyway.
Bottom line: GST is the same in principle as the DT tractor, they just use a hydraulic actuator to eliminate the need to stop the tractor and clutch into a different gear. It is 100% better at loader work than a straight clutch machine. If your mowing large open areas or other tasks that don't require change of direction much, I guess the DT would be ok.