I have a 5035HST and pull a 7' HD cutter. I mow in mid range. When you start up the hill, bump up the throttle a little, or drop it into low and go full on the pedal. As mentioned, driving an HST is not the same as a gear tractor. Pushing the pedal increases the flow of the HST to go faster, which is like going to a higher gear on a gear tractor. The problem here is that pushing the pedal is NOT like pushing on the gas pedal (you're not adding more fuel to the engine to increase engine output).
Use your cruise control, set your speed and then when you get to a hill, instead of mashing on the pedal, use the throttle lever as needed.
Took a little getting used to at first because it really is not intuitive in that sense. It's just a matter of time and getting used to it as your hand is now the "gas pedal" and your foot is the "gears".
I mow in mid range, up some decent inclines at near full speed for the range without any issues.
Now that I think about it, I kind of almost wish there was a third pedal for throttle, that way I could set level ground throttle RPM on the hand lever, set range and HST cruise speed, then use the throttle pedal on the hills as needed...heck, I might even be able to rig that up.