It certainly wouldn't break it. But, it does magnify all the issues of someone missing an attack roll with a maneuver. Then again, if it's one attack roll, then the reroll options like Lightning Recovery are available, so that's a plus.
Personally, I'm partial to the way Star Wars Saga Edition did Whirlwind Attack: the prereqs were a lot lower, and they made it into an area attack, which the way that system worked (no saving throws, just "attacks" against defenses), you still did half damage on a miss, provided you hit "AC" 10. I'd love if there was some way to implement that in 3E as I think it was a semi-useful feat there.