If it's a new tractor, the manual will sometimes give you implement guidelines. The 5hp per foot rule is probably pretty accurate, but like others have said, weight is a big issue too.
I'm currently looking at rotary cutters for an L3800 and I'm waffling back and forth between a medium duty 5' or 6'. There's about a 125# weight difference between the two (for the brand I'm looking at). I've found the horsepower vs. width becomes more important with deep thick grass, as that seems to bog a mower down more than cutting brush or stem weeds.
The extra width helps with getting close to fence lines etc, but limits the maneuverability and the added weight might make the difference between having to leave the loader on or adding some suitcase weights. Everything has a trade-off.
In some cases, the time it takes to cut a field gets offset by the groundspeed you can cut at. Example: if you have to decrease your ground speed to keep from bogging down a 6' cutter, you probably didn't gain any time from running a 5' cutter at a faster ground speed.
I'm kind of in the mindset that I'd prefer a heavier gauge (weight) mower at the sacrifice of mower width, therefore I'm leaning towards the 5' in my case. The heavier mower should last longer and give me more versatility in cutting brush and clearing land.