I don't see WDW removing mask requirements until:
1. Parks have capacity available that is going unfilled
2.
Disneyland is fully open
3. There aren't gray areas in the rules. (masks required in indoor spaces but not outdoor, required in crowded areas, etc.) It's too difficult for cast members to enforce otherwise.
Hope for the best and plan for the worst. Anyone planning for a trip before October should just assume that masks will be required IMO. It requirement may be removed before then but that should be a surprise instead of an expectation.