OK, I've only used my
Woodmaxx at the lowest cut height setting, where it came from the factory. However, I had a Caroni flail for 5 years and used that at a couple different heights, and on both mowers I also sometimes mow with the mower held in the air on the 3pt because the grass is simply too thick to mow on the ground. What I find is this:
1) Mowing at the lowest height produces the best cut quality. You do get a "waffle" or stripe effect because the Y-shaped knife sets don't mow at exactly the same height across the mower width. I don't find this objectionable, but it doesn't look like a putting green.
2) Mowing with the flail held in the air, maybe 6-8 inches above ground, produces a relatively poor and erratic cut quality - no surprise there. The only use for this is when your roller-adjusted height produces bogging.
3) I'm trying to remember because it's been 3+ years (probably 5-6!) since I used the Caroni at a higher roller-set height, but from memory that works OK but produces a less even, less manicured quality than setting at a low height. Still better than a rotary cutter (brush hog) but not terrific.
Someone who wants a great looking 5" cut height needs a finishing mower. The flail can produce a rough cut at 5" or a rather fine cut at 2". In my experience.