I figure, it will get done late in the process, but it will get done. The main reason being: neither side has many other or better options. The Bruins are committed to Swayman, it's not like they can pivot to somebody else without taking on a lot of risk this season. Swayman is not a UFA, he can either play for the best contract he can extract from Boston or he can sit home and not get paid. They'll battle and haggle and eventually wind up at a deal neither side fully loves, but that's often a decent outcome.
The chances that this ends up as a 2 year bridge deal seem high. If the concern is that Swayman doesn't have an extensive NHL resume, the shorter deal mitigates the risk with that. Of course, you're back at this again in 2 years and Swayman is probably in a stronger position. A bridge deal gets Swayman a big raise and he can ask for more, if things go right, in a few years.
I'd rather see him signed long term but I have to admit that it does give me pause to give him big money (to me, meaning $8M+) long term until we see him in action for a full season as the true #1. If he's serious about setting the market for goalies going forward, I'm not fully onboard that he's at that point in his career.
I primarily hope this doesn't eat into most of his training camp/preseason time - is it known whether Swayman would hold out? Don't need a Jordan Montgomery situation.