"1) Floating Winch Handles."
I know someone who bought a nice fancy two-hander. And dropped it overboard while trying to claw upwind and make time one afternoon. They looked at where it had last been seen and said "Oh *&@#" and when I asked about going back for it, said "And can you still see it? Forget about it." cursing for some time about the price. If you can do an effective MOB drill and search grid for something that small...yes, they float.
Bahamas? Calm water? Maybe better. You might want to check out a dive shop, they sell marker buoys for things dropped overboard. Bacically a bright floating spool with 100' of polypro on it and a sinker. Keep one in the cockpit coaming and if something goes overboard, throw the marker buoy fast. Makes a good reason to dive there.
Personally, I think any crew who drops a winch handle overboard and doesn't immediately shout "MAN OVERBOARD!" and lunge for it, just isn't trying hard enough.
"2) Submersible VHF. " They are all rated to a certain depth and time ONLY. They are not "waterproof". I did toss my waterproof binoculars in the sink once to see if they'd float, while they were under warranty. And that's the trick. If the warranty says submersible, the maker will eat water damage during the warranty period. That doesn't mean you should use the radio in the pool. It does mean the radio without that rating will fry faster in the rain.
"3) Life Raft with Hydrostatic release."
Well, those hydrostatic releases on all sorts of things are not there for everyday use. They are there so that if the crew hasn't gotten around to deploying the raft and the boat is going down WITH IT, you've got some chance that it might come up free. Without the release, you've got no chance. So, sure, I'd like that. But I'd settle for a plainer raft, stowed in the cockpit so I could grab it with me.
You might check out Doug Ritter's web site, www.equipped.org, about aviation and marine safety equipment mainly. He's actually done a batch of testing, including life raft testing. Some interesting stuff there--like reports from folks who actually have ditched, and lived to speak about what does and doesn't work as planned.