I was winging with a friend on his Naish 4.6 yesterday, crazy difference speed. I could smoke him on every reach, he was about 30lbs lighter, on a 50L wingboard, granted he wasn't on a HA foil. In comparison, I was on my 115L SUP foil board on my GL180.great review kaser. Agree wholeheartedly about the overpower vs underpower thing....better to have to spill off excess power rather than frantically pumping to get up. My 51yr old arms can manage about 10 minutes of that, then this wingding is just too heavy to hold up. Man o man am I jealous of the wind/wave spot potential you have on a small island in the middle of the ocean. Kinda like new zealand, in a 2 hour drive it's always windy / wavey somewhere from any given direction. Here on vancouver island we're spot starved and limited swell window. Ah well, we have other benefits.
Hdip: will be stoked to hear your progression! I think your 4.8 will be really challenging, especially if you don't have hooks/straps. If I was you, I'd be looking to borrow someone's sup foil at least for first 5-10 learning sessions. But maybe you might consider some stick-on straps, if not put in some strap plugs. I haven't tried with straps yet, but I am looking forward to finishing my new DIY surf foil (5.0), i put in some inserts for foot hooks, will be interesting to see how it is with wing. I am quite sure water starts will require lots of wind (just like windsurfing, need that pop to get up). Also, regular foot will be a lot easier than goofy ... that's a challenge with winging for surfers, have to learn to ride wrong foot forward...which is awkward enough on the water surface, but way more variables to figure out up on foil!
In regards to wind/wave here on Maui, yes you can usually find wind somewhere here most days but can't always match that up with waves. Maui has some heavy shadowing from other islands but the most exposed as most know is the Hookipa area that is the windsurfing capital of the world most say. Which means it gets crowded with windsurfers so we have to go elsewhere. And most of the other spots are dominated by kiters and older windsurfers, so we are the new kids on the block trying to carve out our own little spot out there. Which is partially why I got the 6m to go out those good spots that the kiters or windsurfers won't bother with in light winds. The foil is the advantage.