Rozier is not worth $20 million/year right now. If he has an outstanding year, he might be next summer, but if he has a poor year he'll be worth way less. Why would we lock him in for his best case scenario now, when we can match anything in July if we really want to?
It makes no sense for us to extend him now unless we are getting a discount, and it seems like he wants to bet on himself this year. There's no chance a deal gets done this week, especially not one for $20 million a year
I really think we can settle around the 16 million per range. 4 years 64 million should get it done. It is Danny's guy. He's secret weapon. His pet project.
I never have a good sense about these salary questions.
Social scientists tell us that happiness increases as your income goes up - but the effect is only significant up to $75,000 per year. I admit I tend to have a certain reaction to players who place money over playing on a great team for a great organization that contends for a championship. I suppose I ought to get over myself...
As for your second point, it's an old NBA truism that GM's (or PoBO's, whatever) have blind love for their draft picks, and, as lovers do, overlook their faults. My take on Danny Ainge is that he's got the good sense (not to mention the wise men he consults with) to cut ties if the price isn't right.
I'm like everyone else, I get attached to certain players. I freely admit that I prefer players who have great joint movement (like Terry), who get up into their man on defense (like Rozier), and who fanatically work at their game (such as, for example, Scary Terry).
I'm really encouraged by the Terry Rozier I saw in pre-season; he's been working on the holes in his game, and was trying that work out in the Charlotte and Cleveland games: finishing in the lane, finding teammates for an assist, and hitting open midrange jumpers.
In pre-season the team also experimented with Rozier and Irving on the floor together, something we saw very little of last season. We shall see; I'm doubtful that that's going to work - but if they could pull it off it would be huge for Terry's future in Boston.