I have run into this situation in the past. I am the director of a department of nine employees and have about fifty others in the field that my team oversees in a way. Being that it's accounting, MW always falls during our year end close. I always register assuming it's going to be no problem if I go and work from the resort. One of my co-workers, manager in a different department but rolls up into the same boss, decided he wanted to start doing MW. One year our boss pretty much told us that he didn't think it was a good idea we were both gone for year end. He also said that in years past it was okay, but not sure it would be okay going forward. I pretty much told him that if that was the case, he would be searching for a new director. LOL. So essentially I am working from the resort the first couple of days each year. Heck, one year I worked outside Starbucks at Disney Springs, out by the water. LOL. I usually will work half day in the morning and then head to the parks, but answer emails while waiting in line for rides.