Well, as much as I know I would feel safer once in Hawaii due to the restrictions, mask and testing requirements, I found myself stressing out about the time, cost and consequence to being there in November before my points expired.
1) Non-stop flights were discontinued from my market route and flight schedule significantly reduced. I had to adjust my reservations to accommodate the new flight schedule, and some inter-island transit options were becoming reduced as well. (It was cheaper to fly to Maui then HNL, than just to HNL.) I started to get nervous about being stranded for a few days and have to scramble to find sudden lodging.
2) Because non-stop flights were discontinued, I was now spending about 4-6 hours on a flight with untested persons, then a few hours in the layover airport, then another 3-5 hours on a flight with tested persons. A test does not equate to negative result, however it implies a lesser risk and perhaps travelers might take more precautions because testing negative is a requirement to freely travel once in Hawaii. I got a little stressed out spending several hours in a plane to the layover city with general mainland/connecting passengers.
3) It seems testing (widely available to the general public) has not yet gotten to the sensitivity to clearly differentiate between infectious person and post-contagious viral shedding. I'm concerned that a test recognized as valid by Hawaii gov't would ultimately prevent travel even if I was not a danger to the public. (Of course, I recognize that we're still learning about reoccurrence of the virus within a previously infected person.)
I know I would love the island(s) during this interim time of reopening. I'm just so concerned about getting there safely and not losing funds or expiring points. I ended up cancelling my reservation because I was getting too stressed about the logistics. I'm so glad there are other families that are able to travel, contributing to the tourism/economy in a way that safely helps families who rely on that income.