My dance group just this month switched from masks-required, to what I think is a reasonable compromise that masks are optional most weeks, but required the first week of each month. This is similar to Josh's point 4 - it means that there are dancing opportunities for everyone, both those who will not dance in a mask, and those who would not be comfortable with others not masking.
In making the change, they sent out a survey asking not just do you prefer masks-required or masks-optional, but would you come if masks were required, and would you come if masks were optional. That made it clear that for either policy, there were people in the community for whom it would be a no-go, as well as giving a sense of how prevalent different feelings were in a confidential way rather than just listening to the loudest voices.
I do also like Josh's point 1 of having a clear criterion for if/when we would change the policy, and I agree that Boston-area wastewater numbers are the best metric I'm aware of to use for that.