You have summed up my thinking and why I have been considering the 5ft bush hog despite knowing the tractor will easily "pull" a 6 footer. I really need the bush hog just for the initial brush clobbering. What I intended to do was to use a combination of grapple pushing, ripping, lifting and as necessary a bush hog backing into the mess to open it up. Once the land is sufficiently clear that I can drive forwards, I can use the flail (again the flail has hammers so should do fine once I can get the land to resemble a rough pasture). It just seemed logical to me that putting the power into a smaller cutter would be more effective when trying to cut heavy brush. But that thought is not necessarily based on experience.
It appears I have my work cut out for me. Toe to toe combat with Mother Nature. And she is well entrenched. I got some aerial photos today taken in 1939, 1972 and 1992 of the land that I'll be clearing/mowing. In 1939 it was a pristine farm. In 1972 there were junk cars lining the fields and some areas had returned to brush. In 1992, the cars were gone (thank heavens) but the brush was worse. The brush today fully covers one 5 acre field so thickly that you cannot walk at all and cannot even see beyond the first bushes. My original estimate was that the land had not been mowed in 8-10 years but now it appears we are talking 15 years minimum. The only good news is that it is all softwood/brush/vines/briar and it is flat.
Ideally I'd probably use a medium duty cutter like the 285 but the economics don't work for me and this is after all a one time 10+ acre task. I'd hope a light duty Bush Hog would survive that and based on my experience with the SQ480 I think it will. Kossetx's suggestion that I use the 480 I already own is interesting. If I didn't need to jump through hoops to get things delivered to the island I'd surely try that first but I may need to take advantage of the truck/trailer bringing my new equipment over to get everything delivered at once.
Thanks for the advice. I'd be particularly interested in hearing from those who have tackled this type of clearing before.