I don’t really see any parallels to the three stars we traded to be honest.
Stone and EK were nearing the tail end of their respective primes, while the team was just entering a full blown rebuild, and Duchene wanted to play for a playoff team finally. Two of them by many accounts didn’t want to sign regardless, and all three wanted premium contracts no matter where they signed. There’s a lot more going on there for a small market rebuilding team than signing a rookie to his first real NHL deal.
Personally I see Wolanin more like Hoffman, where we signed him to a show me deal, he showed us, and we signed him to term. So long as Wolainin’s GF stays cool with Tkachuk’s GF, I don’t see there being much of a problem to see what he can do for two years, and then pay him accordingly.