JCS_in_KY...
I have a 6' on the same tractor as you (not sure if you do, but I have the 8x8 trans). 90% of my grass is clean, but I think cutting green thick grass is harder on the units then going into brush (in Froida anyway). Point being I have loaded the tractor a few times, BUT it was always on the 1st pass. So all I did was take my 1st pass and make it around 4' then all the other passes were at the full cut, problem solved.
I also wanted the wider cutter "thinking" I could get up to my fence line, still the 6' can't get that close (just to close not to hit something) so I still have to take the 23hp rider and do the fence line.
I guess what I am saying, YES go for the 6'. If anything you have to take a half pass here and there. You can make a 6' mower smaller, but you can NOT make a 5' mower bigger.
EDIT...Side Note, Like I said above I have a 8x8 trans. I am in 4th gear Low range when cutting. When I am cutting, I set my PTO rpms in the HIGH yellow mark on the tac, if the tac goes down "below" 540" I shift to 3rd, far and few between am I going down one gear.
Also, My Kodiak is a light duty mower, there is NO weight problems at all. AND what is nice about the Kodiak mower, it has openings in the front and back to get rid of what ever it cuts.