Are you sure you'll have temporary Globalist from your trial? The trials they give for status matching typically gives Explorist.

With that being said, you're extremely unlikely to get a suite upgrade at the HR Maui during those dates. I've been trying to book suites for those dates with cash for the better part of the last month and haven't been able to find any availability.

You'll get the same free parking benefit at both the Regency and the HP, so I wouldn't factor that in. Breakfast at the HR Waikiki seems somewhat alright, it's just a daily breakfast sandwich and a juice. Edible but nothing to write a blog post about. I'd check in with the HP as to what they are providing for breakfast, HP's tend to be pretty terrible during covid.