I don't think it's going to be a quick process. It took a full year before the Rangers traded Zuccarello and Hayes after their rebuilding letter. They had no reason to keep them for those 12 months, but they ended up having to keep them for those 12 months. Trades are not easy in a hard cap league.
Kopitar - has to want to leave, going nowhere.
Kovalchuk - has to want to leave, that extra year hurts value, and with anyone but WD he might play.
Brown - still has 3 years left on the contract, and he'll be 35 in Nov.
Carter - still has 3 years left on the contract, a couple months younger than Brown, but just an awful season in every way.
Toffoli - you're selling low before next season starts, so little reason not to keep him and see if he can increase his value as a rental for the deadline, there's no rush.
Lewis - nobody needs Lewis in Oct, so he's a UFA deadline trade.
Clifford - nobody needs Clifford in Oct, so he's a UFA deadline trade.
Iafallo - he'll get his contract, and play somewhere on the top 3 lines.
Grundstrom - he'll get a chance.
Kempe - he'll get his contract, and play somewhere on the top 3 lines.
Wagner - might have a spot to lose.
Leipsic - I guess who knows at this point.
Brodzinski - I guess who knows at this point, but he's free to find a place to play if it's not here.
Doughty - has to want to leave, going nowhere.
Phaneuf - future cap hits don't necessarily matter, but the question is do you buy him out and leave him on the books for 4 years, or just wait his contract out for 2 years? Do you wait to buy him out in June 2020? There's no expansion issue. Whatever they do with him is whatever. There's no real good option, there's no necessarily bad option, so whatever.
Martinez - the easiest player to trade as of March 23rd, 2019. Keep him, trade him, either way.
Forbort - nobody needs Forbort in Oct, so he's maybe a UFA deadline trade.
Roy - seems to have a chance at a full time spot.
LaDue - still signed for cheap, and still hasn't proven anything one way or another.
Walker - seems to have a chance at a full time spot.
MacDermid - I guess who knows at this point.
Quick - still has 4 years left on the contract, and already 33. I'm firmly in the camp that says it's not going to be easy to trade him because of the contract and age. It's been a while since the best big game goalie in the league has either won or played in a big game. You can say that's not his fault, the Kings haven't been all that good, but does that tip the scale toward him being a system goalie? If so, who needs a regular system goalie locked in for 4 more years at a $6m cap hit when he's already 33 years old? There's no former team to save the day like in the Luongo situation.
Campbell - if you want to trade a guy at the height of his value, instead of holding onto him too long and letting his value sink due to an increased sample size and/or a larger contract, you trade Campbell this summer, and Petersen gets the full time backup job, and his ice time increases over time as Quick just gets older.
I think the ball will get rolling a little quicker by the 2020 deadline, but my guess is not too much will be different in Oct 2019. Nobody needs old and overpaid players. The league is either getting younger or it isn't, and we all keep hearing that it is. As usual, it's not even the age, it's the term. You could easily trade Carter or Brown if they had 1 year left, or even better, were already going to be UFA's this summer. If people are thinking Kupari is going to make the team next year, or if they get a top 2 pick this year, or somehow Vilardi actually steps on the ice ever again, my guess is it's the Leipsic's or Brodzinski's that are shown the door and allowed to walk, over somehow getting rid of Carter.
My thought process is always assume(because we're not in the GM office) the easiest move will be made first. So if there's a choice between a multi-year buyout, or letting a marginal player walk in free agency, more likely than not, my guess is you'll see the marginal player walk before the buyout. If the league is getting younger, the odds of trading older players with 2, 3, 4 guaranteed years remaining on a deal are decreased. If Blake can manage to clean house this summer, I'm not against it. I'm just not expecting it.