I recently purchased a Bush Hog 285 (5'), which is one step up from the standard Squealer (?) model. I thought it was what I wanted; dry painted, 120 hp gear box, thicker deck metal, taller sides, just overall heavier duty. The dealer asked what size tractor I owned, and when I told him- TC33DA, with fel, he commented that the tractor would have it's hands full.....he was right! I also use a Quick hitch which throws the cutter approx. 6" further back. It isn't a problem, but I would not want any less tractor weight, or more cutter weight. I wouldn't even try to cut without the fel bucket. While I like the heavy duty stuff, the dry paint was what I was really after, about all I do now is cut pasture.
In the process of trading, tractors and tools, moving up a few hp, and going to 6' tools. I went back to the Woods Brush Bull; due to it's design, the Woods will shed the cut grass off the top MUCH better than the Bush Hog. I also previously had Modern, which is built like the Bush Hog. I think all three are good cutters, the decks rusting out was the reason for replacement (the Woods did last about 1 year longer). If I wasn't cutting in mud, they seldom got washed, but sweeping grass off the deck was necessary for the Bush Hog & Modern.
Heard of the slip clutch "locking up", after a few years, and non maintenance, (which is one of my faults) for that reason, I preferred the shear bolt shaft. The 285 only came with a clutch, so I kept my old shaft off the rusted Woods, but never installed it. Don't even know if it would swap.