Not to be argumentative, but you didn't really address the point that was being made. Are you planning to be masking for the rest of your life? Because, as
@DisneyCane said, it is unlikely that we will ever see transmission levels lower than they are right now.
It's situational.
I didn't wear one when at the brew pub for any part of the experience. Although, it's rare that I eat out these days.
I would like to see the daily transmission rate under 5/100K. We were close, but the last week we've been trending up and the county is back above 13 based on NYT. The CDC has us at 80/100 for the 7 day average. Matching the daily, I would like to see that closer to 10, at least under 50. I'm not ready to assume we'll never get there. Never is a long time.
When I'm at a business, I'm looking at the crowd size, ventilation, space size, and what the employees are doing. If the checker at the cash register can wear a mask for their entire shift to provide service to me, I can wear one for the shorter time I'll be there. That seems like the polite thing to do. When I see others in the store without masks, that's fine too. They do them, I'll do me. They likely have a higher metric in mind to need a mask.
We're going to stadium sporting events in a few weeks. In the past, and now, I'm not planning on wearing a mask generally in the stadium. The real question will be about in the bathrooms. Those are a relatively poorly ventilated space, crowding, and lots of random people. All things that increase risk. On our current trend, if we're 15+/100K daily, probably wear a mask to use the restroom. The stadium restrooms, concourses, and seats all have different risk profiles, hence different reactions.
We're going to WDW in the summer. Orange County FL is at 8/100K daily and 57/100 7 Day Average right now. If our trip was next Tuesday, we would probably still wear masks on shared transit. Not sure about indoor queues. Probably just not do table service dining, which we don't normally do anyway so it's not really a change. If the numbers are lower 2 months from now, then it will not be a concern. If the numbers are higher, then probably in areas with poor ventilation.
It's not a time thing. It's not a "it's been long enough we're done" thing. It's an environmental evaluation. If the environment includes more risk, we take more mitigations, if it includes less then less. The concept or using a mask forever assumes that the risk profile never get's better. Which is unlikely. Given enough time and population change, the risk profile will change. As we covered above, it's not even a single thing now but changes all the time.
People wear bike helmets when they ride. They wear better helmets when they ride riskier bikes. From a 10 speed to a moped to street bike to a racing bike. That doesn't mean they wear the racing bike helmet all the time when walking around. It would give the best fall protection, but be incorrect for the risk profile.
None of these are absolutes, they're all situational and nuanced. We live in a world where the risk of virus transmission from others is higher today than it was in 2019. That doesn't mean it will be forever. It could get worse, could get better, it could stay the same.
People on this forum probably know better than the WDW employees where all the stuffy, crowded, poorly ventilated spaces at WDW are. All the places that cause over heating and smell of sweat.