If memory serves me right Gaudreau also didn't sign until middle or late July as a UFA though; since he walked away as ufa. both have same agents.
So yea i expect this to play out all summer long, then when season starts they will stop negotiating because "I don't want contract stuff to disturb me in season, i just want to focus on playing" simply put.... If by the season opener the deal isn't signed, Willy is either getting traded (don't think we will get a good return for 1 yr rental unless it is sign and trade but now sure how sign and trade will work either with teh cap); or he is walking directly to the UFA market and going to the highest bidder
Given Treliving's history with Gaudreau and Gross I think Tre will be more proactive instead of reactive. At least that is my guess based on some of his takes in the interviews he has done i.e. "lessons learned"