My kids are getting used to masking up when we go places (especially when we visit their grandparents for an outside more-than-6-ft hangout). My 8-yr old daughter didnt like her first one but the second she is pretty happy about wearing (I think she sees it as another fun accessory). My 5 yr old son doesnt like the second, he likes the first, its so loose though... I am still trying to find one that fits him decently.
They understand the mask is the trade off for things they want to do (see grandparents mostly, but hopefully soon other things). That said we're wearing them for maybe 30-60 min, mostly outside in our cool MN spring weather. I don't know about wearing them all day, either, even if it's good weather.
We never go to Disney in summer anyway because we don't like the heat... so mask wearing in the heat is just not gonna happen because being there in the heat even without the mask isn't gonna happen.
I think the all-places-mask idea just recognizes that itll likely be difficult to be 6 ft away from other people outside during certain times of day. Given human nature, it's just easier for everyone if there is a clear directive (wear a mask) than to be like, wear a mask, but hey if its early morning and you're by splash mountain just hanging out and no one else is around that's OK but if its later in the afternoon and people are there you really should, you know, please?). I am quite curious how enforcement will go - so in that situation when there aren't many people around, if we take the masks off for a snack break are we ok? What if we take them off just to chill for a little while? Is it gonna be like, no mask and we boot you out of the park instantly or more flexible?