Sorry to hear about the bank delay.
Yep, Dom's is the only place on Oahu that sells Enfields, and TC is a pretty good guy.
I would recommend not taking H3, high grade and everyone is in a hurry. The bike will be a little rough the first couple hundred miles, and u don't want to push her. I took the Pali with no issues but the Likelike is good to. Best bet is taking the 72 around the east side, weather depending. No Real big hills, Great ride.
i had my bike broken in in 3 days, a good trip around the north shore puts miles on quick, and u know what traffic is like up there on a weekend, so no need to go speeds over half throttle.
Feel free to hit me up some weekend if u want some company.