Just thought I'd jump in. I have a
B7300 HST, which is about half the HP as the tractors you guys have (yes, I'm jealous /forums/images/graemlins/grin.gif). I cut some pretty nasty weeds and grass (6' tall isn't uncommon for my first pass each year) on some pretty steep hills with a 4' cutter. Back in the day when the property was less tame I used same to clear areas with trees that were at least 2".
I know that I'm speculating here /forums/images/graemlins/blush.gif, but I watch my neighbors with larger tractors and they handle 5' and 6' decks quite nicely.
So if it were me, I'd go with a good 6' cutter. The idea of getting a 5' heavy duty then a lesser 6' is great from an equipment standpoint but more costly. A good cutter can stand up to heavier duty work than it is made for as long as you don't require it to do it over and over again.
The wider the cut you make the fewer passes it takes and if you have a lot of area to cover even a few inches makes a big difference in how long it takes to mow. I have a few areas that are tame enough that I can mow them with my 42" JD, but when the 48" slasher is on the tractor I use it because it takes a lot less time - with only a 6" width advantage.
As far as having to go more slowly on hills, I kind of like that for two reasons. First, on a hill slow is good. It is amazing what interesting things like a new hole or bumps can pop up as the land changes and my place can be scary steep /forums/images/graemlins/ooo.gif. Second, the "slasher" works better when it can spend a bit of time whacking the brush. When I go too fast I get a much sloppier cut than when I move more slowly.
Anyway, I'm of the wider is better school of thought. Like I said, I don't have the direct experience with the larger tractors and I could be dead wrong /forums/images/graemlins/confused.gif. If I had your tractor I'd definately go 6'.