Sounds like a great sail! But equipment problems are not fun.
My experience here in Hawaii is to try to double protect everything. I buy a good waterproof Marine Radio and then place them into waterproof bags that I mount to my PFD and can use them while in it. On a long or difficult trip, I carry a spare.
Get a good GPS, then seal every unused port or opening with silicon adhesive and fill ports I want to use with dielectric grease. Or, bag it.
Leash EVERYTHING! Inside and outside the boat. Inside, anything you put in a hatch probably won't be where you can reach it when you need it. Outside, anything can and will wash away when conditions turn bad. Even as you found, leash parts that may want to disconnect and leave at just the wrong time. I'm even a fan of captains (surfboard) leash.
If you NEED a paddle, bring two. Same with anything you rely on to get back safely. I carry a second Mirage drive, especially when we go miles off shore.
It's a lot more fun, even when conditions turn marginal, when you have less to worry about beyond the conditions at hand.
Keep up the good work. Maybe next time some pictures or video
- - - - - - - - - - - - - - - - - - - - - - - - - - - 2007, 2009 & 2010 Hobie AIs and a 2010 TI