If it were up to me, my deadline approach would be as follows...
If I could add a first line center at a discount I take that chance. I know it doesn't make the Bruins a contender this year, but it gives me hope they could contend next year with a good off-season. Pettersson, Miller, Barzal (even though he's played RW since they got Horvat), even Mittelstadt, they all have warts but they also have immense talent.
Failing that...
I would move Carlo for a young center, maybe a guy who's struggling the last 2 years like Cozens/Zegras, or a guy who was projected to be a top6 but hasn't popped yet, like Sillinger, or even an NHL ready prospect like Del Bel Belluz. There has to be a fit somewhere along that spectrum.
Then I'd move Coyle under similar criteria, but this time I'd be looking at defensemen. I think Coyle would be sought after in New Jersey and Vegas and they're probably not on his no trade list. I'm not looking for a star here so Seamus Casey in NJ is probably a reach, but someone like Kaeden Korczak in Vegas could be a good fit. Big, strong, can skate, moves the puck well... Kovacevic is also an option if they don't think he's critical to their playoff chances. Both teams have the cap space.
Freddy goes if he wants more than $4m and isn't signed by 4Nations. (I think Frederic will want $4-5m.) I would like to think a reasonable return would be a 2nd and 4th but we've seen 'gritty' guys go for more.
I keep Geekie. He's the same age as our core and I think he'll outproduce his next contract. I also think it would cost a lot more to replace him in free agency. At worst, I think he'll be worth more a year from now and at best he'll be too valuable to trade (if he cracks 30 next year).
I'd probably keep Brazeau too. He's not going to fetch much in trade and he's not going to be expensive to re-sign. I think one of the big mistakes with this team this year is that there was no competition for jobs. They didn't have the cap space for it and the kids didn't have great camps. Brazeau and Wahlstrom (if he's not waived) can push guys for jobs in the fall.
I'd see if there's a market for Korpisalo and give DiPietro a shot in the NHL. Korpisalo has had a solid season and would upgrade the tandem in Utah. DiPietro is a UFA at the end of the season and I'd like to find out if he can be a backup here next year, or if we have to sign another veteran.
Marchand is a tough one. I don't want him to go and I'd only move him if I thought my chances of getting him back were better than 50/50. I guess it would be negligent not to see what's out there in terms of offers, but the two most likely destinations, Colorado and Vegas, don't have 1st round picks or even particularly good prospects. Would Colorado give up Mittelstadt for him? If the return isn't great I'd rather keep him.
Ideally, Plan B would add two NHL players (F & D) to the lineup. It would give us a 2nd and 4th for a full slate of picks at the draft. And it clears $12m which gives us about $32m in cap space, plenty of room to re-sign our RFA's and to make a big offer to Rantanen or Ehlers.
I'd also get Lysell up for the rest of the season to let him get comfortable and see if he can be a middle6 winger for us next year. (I think he'll be up regardless.)
Lastly, I let Sacco and the whole coaching staff go and bring in the best young coach I could get. It takes so long to teach a new defensive system... I bring that guy in now so they have 25 games to lay the groundwork and set the plan for the off-season.