Look back in history and give me an example of one negotiation that was executed this way. I'm sorry, but what you're saying right now is the rosiest outlook you could possibly have. Leaf fans said the same things about JVR and Gardiner.If they're in contention at the trade deadline they can still trade him... they'll know whether or not he is going to sign before that anyway.
Competitive teams don't trade away offensive drivers mid-season. It causes too much disruption.
Hall is New Jersey's Kawhi right now. Except instead of being on a highly competitive roster, he's on the team that won the draft lottery.