1. Can Braden Holtby replicate (or even top) the success of his Vezina Trophy-winning 2015-16 season, and how important is it that he do so?
Over the past two seasons, Holtby has put his name into the mix as one of the League's elite goaltenders, cementing it by bringing home his first Vezina back in June. There's no reason to doubt his ability to repeat his success from last year; in fact, there's reason to think that he can improve upon it, especially considering that he's only 26, and just entering what should be his peak seasons.
Holtby got off to a tremendous start last season, but saw his game decline a bit after the new year - and yet still ended the season with numbers that kept pace with his overall career stats. He doesn't have to exactly replicate what he did during the first half (and may not be able to do so) but if he can come close, and maintain that level over the course of the season, he'll be well on his way to getting his name in the Vezina conversation once more.
How important is that consistency for the team? It's pretty important, although perhaps not as important this year as it would have been last year. The Caps are coming into the season with a lineup which, on paper, could actually be better than last season; they'll still need Holtby to have a strong year overall in order for the team to succeed, but they'll still be in the mix for the Division title even if he slips a bit.
Where his performance becomes vitally important for the Caps is in the postseason. Holtby has put up sparkling playoff numbers over the course of his career, and yet has been outdueled whenever the team's tried to advance past the second round (most frequently by Henrik Lundqvist, most recently by Matt Murray). That's not all on him, of course, and an injury this past spring held him back against the Penguins, but he needs to maintain his consistency - and stay healthy - for the Caps to finally get over that playoff hump.
2. How much of an impact will the additions of Lars Eller and Brett Connolly have on the team's bottom six?
This summer's big acquisitions could potentially have a huge impact on the team. Consider that last year, the Caps put up one of the best seasons in franchise history with what was a pretty weak bottom six that at times overachieved; that weakness was brought into stark relief against a deeper Penguins team in the playoffs, and eventually cost them the series.
So GM Brian MacLellan did what he's done for the past two offseasons: he identified the problem and addressed it head on, making a draft-day trade for Lars Eller and then bringing in free-agent Conolly to shore up the forward depth.
Now, a season after finding a second-line center, the Caps have a bona fide third-line center and a depth winger, both of whom have a little something to prove in their new roles. Neither is going to be the Caps' answer to Phil Kessel, but they do provide the team with more options, more skill and a more balanced attack throughout the forward group.
3. This is the second year of the team's self-described two-year window to win a Cup; is the window really closing?
To some extent, yes. It's not slamming shut, of course; the team still has plenty of talent in the pipeline, and the core players - guys like Alex Ovechkin and Nicklas Backstrom and Braden Holtby - are all still locked up for the foreseeable future. But when this season ends, there will be some huge decisions to make that will likely change the way the team looks next year and beyond.
For starters, both Justin Williams and T.J. Oshie are set to be unrestricted free agents on July 1. It's unlikely that the team will be able to keep both, and there's a chance both will walk, which means in one fell swoop the team's top-six forwards will take a huge hit.
Even if they wanted to keep one or both, the ability to do so will hinge largely on what kind of deals (if any) MacLellan is able to get for impending RFAs Evgeny Kuznetsov and Andre Burakovsky (to say nothing of Dmitry Orlov and soon-to-be UFA Karl Alzner on the blueline).