I've got a five footer on my tc29d right now. I spent three hour mowing a neighbor's horse pasture on Saturday. In sparse to medium grass, even pretty tall, was running pretty fast. In places I was at full speed in medium range at almost WOT. In thick dense grass, I was going pretty slow to avoid bogging. Sierra foothills makes me guess that the grass is pretty thin compared to the Midwest (I could very well be wrong, though). I think you'd probably be fine with a six footer as far as the cutting goes, but I think your machine will be more stable with a five foot model.
My tractor has loaded R4s on all four corners. I don't have a loader, but I had about 100 lbs of weight hanging off the front. I don't know the model of my mower, but it's a light or medium duty cutter. This machine is new to me (I've put about 50 hours on it), so I'm not real familiar with its slope capabilities, but i can definitely say that I wouldn't want to suddenly lift the mower while on much of a side slope. These tractors aren't very wide, and especially with a loader on, they center of gravity is relatively high. I think you could be happy and mow at a little slower ground speed with a 6' model and some wheel spacers, or you could save some money and go with the 5'.