I don't get re-signing Dillon, and I don't get why people want to dump Kempny. Both of those are linked for me, because if you're re-signing Dillon, you almost have to move on from Kempny. So any savings from moving Kempny are swallowed up by the Dillon contract, since you need to pay him 3.75-4.25m a year for 3-4 years to complement Carlson. The problem with choosing Dillon over Kempny, regardless of the stylistic fit, is that how much of an upgrade is Dillon over a healthy Kempny? Fit-wise, Dillon might allow Carlson to take on harder competition, but I actually feel like Reirden got Carlson's deployment mostly correct - play him big minutes in an offensive role, reduce his defense/PK role. He certainly can perform both of those duties (play toughs/PK), but you'd rather he create offense, since our other defensemen can cover those duties but can't create offense.
I think the biggest dilemma GMBM has with the d-core is defining the roles of our two legit t4 D. What happens if you play Carlson/Orlov together, what happens if you separate them. Who plays harder competition, who gets offensive zone starts. Carlson and Orlov work as an offensive d-pair, but then we have no depth behind. So you separate them, but that means any defenseman who doesn't work with Carlson moves to the 3rd pair, unless they can move to their offhand. That might lead the Caps to try to sign TJ Brodie, since he's worked on the right side of a pairing with Giordano, and could presumably play on the left side with Carlson. If you sign Brodie, you do probably need to move on from Kempny though.
Dillon is a fine player, but he essentially has two possible roles - top pair complement, or 3rd pair PK guy. If he's the former, how much better is he than a 2.5m (healthy) Kempny? If he's the latter, how much better is he than a 1m Siegenthaler? Is the upgrade to paying him 4m for either of those roles worth it?
Dumping Kempny only saves you 1.7m at the most, and the Caps don't need need that space (unless they go big game hunting in FA). They have 9m in space, and need to sign Boyd/Siegenthaler to RFA deals, and could sign a 1b goalie and a t4 RHD. Unless they're targeting Pietrangelo, they don't need to shed money. I feel like you almost need to give Kempny another 50 games or so to see if he can again play with Carlson on the top pair. If it works, you've given yourself 2 years to let Fehervary/Alexeyev mature to replace him. If it doesn't work, you rent a replacement at the deadline, since Kempny's cheap salary lets you bank space.