Given his relative inexperience, and the fact that the boat is new to him... or relatively new to him. Add into that mix a new piece of gear he has never used (the Monitor Windvane) and the difficulties that crossing the Gulf Stream can present, it doesn't make much sense to advocate a straight bluewater shot to Bermuda for him this year.
He really should get the windvane and then sail with it for a few months and learn how to use it in different conditions. He should also spend enough time on his boat that he has complete confidence in it. Doubts and fears can be real troublemakers,
and if he doesn't have complete confidence in his abilities and his boat's abilities... he needs to work up to that point, prior to making a long, single-handed bluewater passage.
Doing the journey as a series of progressively longer coastal hops, followed by a relatively short bluewater passage is going to give him the experience, and help him have the skills and confidence needed for the longer direct bluewater passage, while allowing him options if things start to get too hairy for him.
While I'm all for "going for it", I don't think it should be done without at least a solid foundation of preparation.
A couple of points... I don't think that Dumas was a valid comparison. IIRC, Vito Dumas wasn't a relative novice, and he had outfitted the boat he used himself, so it wasn't really an unknown quantity to him. Granted, his equipment was a bit on the primitive side, compared to what we have today, but the boat was probably considerably overbuilt. He had also had 15-20 years of experience sailing before doing his circumnavigation in the Legh II. The Legh II was also a purposely built bluewater passage maker... not a lightly built coastal cruiser.
In 1933, Dumas commissioned Campos, who was famous for hisdouble-ender types influenced by Colin Archer, Atkins, and local native craft which had originated in the Mediterranean, to design and build a 32-footer expressly for ocean voyaging.(8) Legh II was 32 feet 2 inches overall, 10 feet 9 inches wide, and had a maximum draft of 5 feet 7 inches the ultimate refinement of its type and very nearly a perfect model. She was ketch-rigged and had 9 tons of iron ballast outside.
Tania Aebi wasn't a very good comparison in many ways either. While she was essentially a complete novice, she was on a brand new boat, that was designed as a voyaging boat, and very capable of handling bluewater passages, not a coastal cruiser, over a decade old and with some unknowns in the hardware and rigging. In bad weather conditions, the Contessa 26 is going to be far more forgiving of mistakes than an O'Day 34.
Finally, just because something has been done before, doesn't necessarily make it wise or smart to repeat it. I am willing to bet that Tania Aebi would admit that she had a lot of luck, and that it could have easily gone the other way.