You have to match the mower with the tractor, and match the mower to what you're mowing. I have a 5ft rotary cutter on my 34HP tractor. If I can run it over, I can cut it, no problem, and I'm probably doing 4 mph usually. But I wouldn't want to do 50 acres with that, its too small. You need to figure the amount of mower you need to cut your field(s), then go from there. If you already have the mower, match the tractor. 1ft of cutting width for every 5HP of PTO power is the general rule. If you have the tractor, this is beside the point, as the best cutter is the one that best matches the tractor. A bigger one won't speed things up because it will bog the tractor down.
I've only skimmed the thread so I may have missed it, but you haven't given us what exactly you're planning to do, or what the equipment situation is. That can take this discussion from hypothetical to real facts, info and help.