This is a great question and one I get often! I think you’re doing the right thing by taking him out! I always tell families that it depends on the resident and how they do on trips. As long as he’s enjoying himself and leaving and coming back to the community without a problem, taking him on trips is a wonderful idea. There may come a time when it becomes more difficult (for example, he’s not wanting to go back inside the community) or perhaps it will always be a nice, easy transition. All I can say now, though, is that you’re doing what’s best for him and for you by taking him on trips.
My only recommendation is to avoid taking him to his old house or anywhere that would cause extra confusion. Many of my residents believe that they still live at home, so seeing their old houses causes them a great deal of stress and befuddlement. Otherwise, this sounds like it’s going really well!