Something I can't help but wonder, and I don't think this falls into the "blame" category here, is if there isn't something to the idea that Dubas being a clever fellow isn't trying to import something of what we're seeing in Baseball when it comes to negotiations where he's not altogether interested in a deal where everyone feels as good as they can about it but rather where he's going to do whatever he thinks is in the best interests of the club going forward.
I've referenced it before but in Baseball if a team can pay a guy much less than market, they do. If they can manipulate his service time, they do. Players don't love it but it's now generally assumed to be SOP. In hockey we've seen almost 15 years now of teams effectively giving players what they want in 95% of cases so as to avoid hurt feelings and, above all else, mitigate the risk of losing players. As such we've seen a pretty constant and steady inflation of player salaries.
Maybe Dubas is trying to buck that trend. Maybe he's inclined to take things to the wire even for minimal returns so long as they're even incrementally better than what he could get going the traditional route. That isn't to say he'll be successful or even that he'll always make the right call about the cost/benefit analysis in a particular situation but I think there's a fair argument to be made that doing what everyone else does isn't necessarily the best practice for a team that will be facing cap issues.