The good: I like the roster. I like that you're maximizing value for some of the Caps' best veterans to keep the team competitive, without getting manic about selling everyone that isn't nailed down. Holtby and Grubauer are each the Caps' all time leader in save percentage, depending on whether you look at the playoffs or the regular season. At least one of them is starting next fall in Washington. If they leave the playoffs in the first round, I could see that just being Holtby.
While Montreal might want other centers more than Backstrom right now, he is a very, very good center, and they would certainly be happy to have him.
The bad: Colorado already have a Vezina winning goalie they got from Washington for a first round pick. They need to build a defense in front of him (Hey, come to think of it, maybe the Caps shouldn't go all-in in a quest to trade for Colorado's defensemen, no matter how good their possession numbers look, since their backup goalie is Semyon Varlamov and they're losing most of their games).
Carlson is signing somewhere for stability. As the best defenseman on the UFA market (if not, arguably, in the NHL right now) he will get a no movement clause and get to sign off on any GM making him sell his house, pack up his things, and start over. That's not a huge issue, but there goes your fourth line. If you're trading just his rights, so Boston can sign him for an extra year, maybe they'll give you a 2nd? Max?
Doughty is staying in LA, and you could certainly keep a younger, more effective player named John Carlson at a lower cap hit. This team is young as anything and it might miss the playoffs.
All that said, it's a lot of talent, and it could be pretty darn good in another couple of years, if its players don't get discouraged.
Still, I think this is a little too much turnover toward inexperience and potential for one summer. If they make this many moves over three years, they might still be in the playoffs in each of those years, which helps the young guys build confidence, and keeps the trade value high on the old guys. I think that's the secret to how teams like Detroit, Pittsburgh, and Tampa stay good from year to year: even though it hurts at the draft, there are other rewards for doing well as a team: your player learn more, get better, and want to stick around, and other players want to come and join your team.
So while I admire the thought process here, this looks like the kind of drastic rebuild that Ottawa are being forced into by external financial constraints this summer. I think the Caps might stay more competitive just by thinking about this summer in terms of homeostasis: making small internal changes to stay the same. They bring up Johansen, Boyd....
if they want to trade Carlson, they trade him at the deadline for maximum value, and get back, say, Shea Theodore, plus picks and prospects, and then they rent a cheap right handed defenseman to help them compete in the playoffs this year.
If they want to trade Backstrom, yeah, they wait until summer. He'll still be under contract, and other teams have an idea of their future plans by the draft. But odds are he'll get sixty points next year. He's such a team guy that his only personal goal each season, even when he was insanely good, has been, "make the playoffs." He's the kind of guy you build a perennially successful team around.
If they want to trade Holtby for just a first round pick, they take a cold shower and see if they sober up in a couple hours.
This right here is enough cap space to sign John Tavares, but if the goal is to have a #1 center who gives you a chance to win any game, then why not just keep Nick Backstrom at a third of the (next year) cap hit?