Are those really guidelines though?
That up to 25 people can gather indoors with no social distancing and no masks?
Or, are the guidelines more layered than that. Something like up to 25 people can gather, with controls around droplet and aerosol transmission between independent contamination groups?
So, sure, have 25 over for Thanksgiving, but do it in a way to minimize cross contamination. Maybe outside, or with increased fresh air ventilation, or wear source control for droplets and aerosols, or combinations of these.
Lots of activities are largely OK, but have little issues. We're planning an outdoor gathering if the weather is good. With tables set 6-10 feet apart for air control. But, there's still bathrooms, cooking, and other indoor parts. For those parts, we'll need to use different controls.
Just like WDW, people that are spread out while walking outdoors probably don't really need masks. There's low risk while those things are true. It's when they're not spread out, or no longer outside. Those things change frequently at WDW. They could have a rule to put a mask on whenever they occur, but it's easier to just have one rule.
I don't wear a mask when I walk the dog. If we pass someone, we move aside and give a large space for a short interaction. When we walk the trails around the lake, we bring a mask and put it on whenever we pass someone or there's a crowd. There's less space on the lake path and more people. I can see where WDW is more like walking a park trail than walking the dog in the neighborhood.