I fly this often.

A passport will make your life much easier sine Guam has its own customs union and a separate VWP and entry requirements. At the gate flying to HNL CBP sets up and processes you right as you come up for boarding.
On arrival into Guam from HNL you have Guam customs, and arriving into HNL from GUAM you get bussed to Customs.

In Guam the darn ol' ChiComs and Russkies can visit without a visa unlike mainland US but they can still buy tonnes of stuff that is Made in America or high end (or even low end judging by the amount of toilet paper and pots/pans from K-mart the Chinese check-in going home).

I bet the K-Mart on Guam is the busiest in America but I digress.

Oh, and HOAs are evil. IMO, avoid at all costs. If it is a nice enough area your property will be fine.