I'm not sure there is much slack to pick up. Local broadcasters put out informational messages, emergency services are active, and mobile cell towers are being deployed. While deadly, the fire itself affects a small area, so you won't hear large amounts of HF traffic in/out of Hawaii.
Hawaii ARES has been activated and, as to be expected with a local disaster, is leaning heavily into VHF/UHF. Their current status is here: https://bit.ly/HAM-UPDATE
We'll probably get reports to read about their part in the coming months.
I use 2mm bullet/banana connectors for my EFHW and linked dipoles in windy conditions. They work perfectly well with strain relief, which can be as simple as a strip of plastic with four holes.
Recently I've been using K6ARK's method of adhesive lined heat shrink: https://youtu.be/HlFXs5kk_8w
Edit: I forgot to say the usefulness of K6ARK's style is that you can reel the whole wire. Disconnect at the length you want and plug your transformer at the link. Keep the reel hanging with your transformer or use the remaining length as a counterpoise.
Another idea to consider is a vertical antenna. 5 meters is a 20m quarter wave and presents decent efficiency when coil-loaded into the 40m band. A capacitive hat could be helpful too, though it is something I haven't personally tried.
If you're looking to use 40, 80, and 160 as local propagation, maybe a linearly loaded or folded dipole could do the trick. You can run it lengthwise or as a fold along the top of the boat. It'll make setup easier and not location dependent.