He may not have had all the experiance in the world but you only get that from getting out and doing it anyway. So at least he was out there giving it a go. He made the crossing and made West End, so he wasn't doing to bad.
Bad is an individual definition. I'd consider loss of engine and loss of primary anchor, no insurance, and a few other things I noticed to be bad for one leg.
As I read it his total experience was a few hours on a friends boat earlier the day he left single handed his first time handling a boat.
I feel bad for him, but I repeatedly see people encouraged to take the adventure, not delay, no training. He took the time to sell everything, to prepare the boat, and to start his blog, but couldn't take the time to gain a little experience first.
Those things that did go bad on the first leg, as well as other things he could have but didn't do, led to his loss of the boat.
Now, ultimately it was his choice and if he went in with eyes fully open and aware of the risks, then that's his right. I admit this is just one aspect of the sailing world and the CF world of adventure which I'd consider foolhardiness that I just don't grasp or understand. Doesn't make them wrong, just outside my comfort zone. There are a lot of them however that don't make it to forums as they don't work out, with far worse consequences than his. There is risk to all boating. I just believe in managing it to a lower level more than some do.