@groth911 - after reading this I followed gdmetz's advice and did so with my player. I already had him at HiA, and he had already played in games... Designated without waivers, then Assigned to HiA. Also, he's still showing three options. Not sure if that will change next season, but it's not a big deal to me.
I agree with you, WiS wording doesn't fully explain how you can use Designate. There's a tendency to confuse it with auto-Release or auto-Waive, it's actually more of a way to manipulate rosters without doing those things.