I feel like there is no right answer here.
First, I don't read too much into Bob's statements at media day. He has always been very direct and concise when handling the media. While not necessarily as curt as he was that day, I don't think his tone or demeanor mean much.
Second, I am an outspoken opponent of giving his postseason performances too much credence. Small sample sizes and the last three appearances have been against Pittsburgh 2x and Washington. But I'll play devil's advocate. As someone broke it down for me - despite Bob being arguably the best goalie in the league (or at least top-3), the Jackets lack of postseason success speaks for itself. Bobrovsky may be part of the answer to winning the Cup, but he isn't THE answer. And the kind of contract he is demanding is one you typically reserve for THE answer. So no denying it he gets 10x8 or more, he will be overpaid.
Third, I think there is an argument that overpaying a few players is almost a necessity in today's game. Whether it be because of the demand for the player's services, the need to attract talent to a team the player views as less than ideal, or as payment for future (i.e. young stars with a rising cap) or past (bridge deal) underpayments.
Fourth, I think Bob can arguably be worth a mega deal if viewed as a one way ticket to the postseason. I think the argument exists that his postseason stats are less than critical given what he does for the team in the regular season. If I were a GM and I knew about a player who basically guaranteed I would make the playoffs each year but then disappeared in the postseason (Joe Thornton perhaps), I would still think long and hard about giving him a mega deal.
So I feel like the Bob situation has no answer. They either massively overpay and keep him (if he will have us, that is) or they lose him. Either way, he is doing the Jackets no favors. But with a player like him, maybe he has done us enough favors already.