I know/hope I will do this sometime, and face the same concerns. Go out of town for the first times. Wear flats or low heels. Check the Weather channel and avoid rain or windy days.
I don't know what type of day out you want, but keep it simple. Drop off mail at a drive by mail box. If you like, park, and walk to the box. Drop off a bag of old clothes at goodwill, and get out of the car to put it in. You can do it, and that is that.
Barbara
