For safety I carry -
Mirror
Whistle
Flashlight
Phone in dry pouch
Bungee and dyneema loop for emergency rudder
(Plus im always in an appropriately thick wetsuit, wearing blaze orange, always use a leash, and have reflective stickers all over everything)
Only on big days I also carry a PLB
I have been meaning to get a VHF radio too, but havent yet. That is very handy to have.
I carry all those things on my PFD. As you mention Dry Box, in a worst case scenario like you're preparing for, it could be reasonably expected that you are separated from your boat with no warning. Ideally you'll have as many of these items attached to YOU as possible.
A friend of a friend tragically died after his leash broke, boat blew away, and partner didnt have a phone. The swimmer had a phone...in the hatch of his boat. Just saying you have the right idea, but always have at least 1 communication device physically attached to YOU at all times in medium-big conditions, in this case your phone.
When bad things happen to experienced people it is usually a chain of failures, so assess where the weak links of your chain are. You're on the right track though.