so desperate for a delivery crew that they would hire that guy.
Yeah. So much wrong, it's hard to know where to start. From an owner's perspective,
-- the boat wasn't ready. Owner should have been aware (or made aware) and made some hard decisions before the boat left the dock. And, for-sure, leaving then having to turn back a few hours later because of problems should have been a big wake-up call before deciding to leave again.
-- the route was poorly planned (and horribly executed). ANY reputable cruising guide - plus the Ha Ha instructions - indicate staying well offshore of the coast until southwest of the entrance to Turtle Bay. IIRC, the Ha-Ha waypoint provided to skippers is something like 15 miles outside the entrance. The entrance is roughly mile wide, and well marked, but the rocks on either side have eaten more than a few boats that tried to cut a corner. Following the 10m contour along there is a Really Bad Idea.
-- if they were having problems (rig, sails, electrical, whatever), the right move is almost always to get further offshore. If hull-integrity is not compromised, sea-room represents time and space to sort things out. NOTHING good ever happens right along a rocky coast. Hell, they had a 20k offshore breeze, according to reports. They could have dropped sails, turned off the engine and *drifted* out to a safe distance. Would have been a lot smarter than turning towards dirt.
-- a whole lot of other decision making was... suboptimal. Like, if you're up against the beach headed toward a rocky entrance, and your autopilot is acting up... turn off the freakin' autopilot and put someone who knows how to steer a safe course on the helm. Problems cascade in a chain, and the farther upstream you can cut the chain the better. Of all things, putting effort into basic safety- and navigation practices (in that order, IMO) is the best option... putting time and effort into trying to fix the autopilot or figure out what's wrong with the electrical system or updating waypoints on the tablet is a waste of time, and probably made things demonstrably worse.
-- and... I'll be cautious here, I know the guy... 15 minutes on social media would have been more than enough of a background check to make me decide to hire someone - anyone - else.
When I was doing deliveries for-hire, I had a contract (*). part of that contract was that I was the "person in charge" for the trip, even if the owner was aboard. I always had the owner put me as a "named operator" on their insurance *and* I got my own insurance binder for the trip. I went over routes with the owner, plus comms-plans (in the days when SSB was the only option), plus bail-out contingencies if I needed to avoid unfavorable weather or address problems while enroute. I didn't usually insist on a pre-delivery survey - the boats I was running were usually professionally-maintained race boats - but I always-always-always did full mechanical, systems and rig-checks, plus all sorts of common pre-trip work (oil-change, filter-changes, battery checks), plus a sea trial, before committing to specific timing. There were more than a few deliveries I turned down because either the boat wasn't sufficiently ready, or because the owner's insistence on a date would have put me in a weather window that felt sketchy.
(*) I did get my license - 100-ton, it helped with insurance - and did log my miles. But IMO, the key bit to all of it was putting enough prep in, up front, to *avoid* sketchy situations. From what I've read, seems like neither the owner nor the "captain" did that in this case.
$.02