Addressing each comment in order. I appreciate the input!

Regarding matches, I'll probably have a mini bic with me. It'll be screwed up by saltwater quickly. I don't prioritize fire starting because there just isn't much land (like, none) from RI to Bermuda. Fire starting would only be needed if we ended up on some desolate area of the easter seaboard, but that seems quite unlikely. I could be convinced otherwise.

I don't foresee being in the water without a life raft, but one so often hears about "X" happening and ending with only what's on your person. IF I end up in the water with my lifejacket and another person I'd have enough stuff to tie us together (safety lanyard/lifting strap).

Headlamp will be waterproof. Probably a Black Diamond Storm, though I'd love something that's waterproof, USB rechargeable, and has an adjustable red light (I can get the first two options but I have to go BD Storm if I want adjustable red light based on what I've seen).

I own a "pocket" flare launcher but I just don't see myself deploying it well/safely from in the water and if I'm in a liferaft, I'll have flares. If I could find a tiny smoke flare I'd consider it.

I think swapping the laser for a waterproof VHF is probably a good and reasonable call.

I will dummy-cord a knife. Probably the leatherman back to its sheeth. Good idea as well.

Thanks again!