I shall gladly abuse your knowledge then, as I much prefer learning from the decisions of others when possible! I believe it is the island of O'ahu, but I am under the impression that island hopping is pretty easy in general.You've got an inch and about 15-20 pounds on me, but I've got about 30+ years on you!
There must also be 20+ easy entry shore dives - most off beaches although a few entries are over lava which will shred your bare feet. My go to boot is a 3MM with a slightly thicker sole.
Thank you all for the advice, it sounds like the mask will just have to be a trial by fire, and that I should go for a moderate weight shoe/boot with a sturdy sole. I have no idea what sites I will dive from, so I have no way of knowing the soil conditions, and a little bit of too much shoe sounds much nicer than bailing on a dive because I couldn't get to the water. I also prefer to make a few changes as possible, so wearing the same size boot with the find will give me a small comfort of familiarity.
Lastly, if you’ll be living on Hawaii, a GUE instructor Meredith Tanguay does classes there. I’d highly recommend GUE Fundamentals when you get to 20 dives or so.
I will definitely look into it once I get some experience!