I think when you are making proposals, you should ask yourself why the other team (i.e. Las Vegas) would be trading the given asset (i.e. Theodore) you are attempting to acquire. Then, ask yourself what the best asset is in the deal is (i.e. in the case of your first proposal, Theodore).
Regarding JVR, he gets you Jack Johnson. He's a pending free agent winger who is prone to lazy lapses, and is predominantly a one-way player. Adding a little sweetner (i.e. a 2nd round pick) bumps it up to Savard.
What you said about JVR is what they said about Kessel until he stopped playing with Bozak. JVR could be 'the piece' on a cup contender too & no one will talk about his defense if he plays with a Selke type center.