(Another) Great post Fair.
Do you not think it's possible that a restriction on accumulating a position in the company would have been included as part of the NDA? I had long thought some kind of provision was already put in place to protect against such an occurance, tied to reasonable timing parameters (and mutual 'first right' benefits) associated with post milestone fulfillment. And even if done by proxy I would think that any violation of such a condition would ultimately be uncovered. While it wouldn't protect against those from outside of NDA it would certainly protect the company from getting ambushed, via buying Pinetree's position as example or otherwise accumulating, no?
As it relates, I would hope that someone is also keeping a close horse-eye on our snake-in-the-grass Shelly at this critical juncture.