"When I am talking to my W about ML, however, I am like a deer in the headlights. I fumble, mumble, get off track, and generally do not make my points very well."
Exactly. I've always got it all planned out in my head. It just doesn't seem to come out right!
I probably wouldn't be so hot in front of a judge, either.
"And yes, writing letters or emails is definitely a wimpy way to make a point."
On the other hand, it's not like I'm trying to avoid conflict. In fact, I'm trying to hasten it. The point of a letter is to get your points out there, uninterrupted. It's a starting point (not a substitute) for conversation.
I like your outline idea. Try some other lawyer tricks too, like loudly shouting "objection" and moving for a mistrial.