The main reason for mowing this field is to keep it from returning to woods, which I suspect it was many decades ago, and which it would be happy to do if left alone a few years. I mowed dozens of foot-tall poplar trees the past couple of days. I mow it in the fall to cut the woody trees, including re-sprouting locust trees that grow to five or six feet tall in a season, while they are still green in their first season.
Mowing once a year would do the job, but also doing a spring mowing cuts down the tall grass and gives the wild flowers a chance to be seen.
I have no interest in a lawn-like cut. I just don't want to leave a forest of 18 to 24 inch stems sticking up after I mow, which is what I was getting with the flail. It takes me around four days (afternoons only - I'm retired for heavens sake) to mow it, so cutting twice to isn't going to happen.
The good news is removing the front guard, the equivalent of raising the front as several posters have suggested, seems to have solved the problem. I got very good results, and good speed, yesterday after I did that.
I really like operating it in the full offset position as I mostly don't have to drive over standing stuff before it's mowed. It also works well to trim up pretty close to free-standing trees in the middle of the field, and is great for getting under large pines and other trees around the edges. The tractor does recognize the side load when going up steep hills -- there is a definite tendency to pull to that side. And of course the whole point of a ditch and bank mower, being able to mow across steep banks while keeping the tractor on flatter ground, is great.