Jackets do need a top 6C, but they won't look at making that move before they know the draft order and it won't involve trading their captain.

Why would either team make this move? CBJ just gave Jenner, their captain, an extension last year and I don't see why they would blow up the locker room for a more expensive player when the team isn't in a win-now window. WSH shouldn't be moving Kuzy since he's one of the top point scorers despite having his struggles this year, and again there is no reason to blow up the locker room and piss off Ovi for a lateral move.

Also Oshie scratched? Seems strange to sideline the one guy that the power play works with, and I'd think they could not overpay either Sheary or Milano to instead let Oshie have his rightful place in the lineup and give raises to Orlov and Jensen (since they could both be big FA targets)

The main idea of the retool is to become a bit younger, of course Oshie can be in the lineup next season (I hope so), but he'll be 37 and with all his injuries, who knows. Also I think Kuzy needs a change of scenary, he looks disinterested to be honest and the Caps need a cap space.
But that's only my view, would like to know in which direction you think the Caps should go.

Kuzy does look off right now, but I don't think trading him at this point would do anything more than anger Ovi and ruin the locker room. As for next year, I would prioritize bringing back Orlov, Jensen, Hathaway, and Strome and let go of Sheary and/or Milano if necessary to open Cap and Lineup space for McMichael and Protas. I'd let Gustafsson and TvR price themselves out of DC and use Alexeyev and Iorio/Johansen as interior replacements, and possibly moving Mantha if cap becomes a large concern.

No way Caps make that CBJ trade.