While I'm following all this with great interest (much more complicated than I thought), I'll report on my hills.

Testing the new bike, I rode up Diamond Head and I was using the lowest gear it had. Diamond Head is not my worst hill (grin).

Another place I have ridden near Waikiki is Tantalus - about a 5 mile climb. On my present bike, I am almost always in the lowest gear (28 front and I think a 32 rear). It's a Bianchi Volpe and kinda heavy - around 28 pounds without my stuff on it. And I guess the geometry isn't as good for climbing but I don't know much about that stuff.

There are a number of shorter hills, but also steeper ones, that I will only ride on occasion, such as riding around the island.