Oh man, I get your feelings on the Jeepster, I’ve been there with some old cars, but it’s like a family member at this point. I would put it in accessible storage for the next year, then see how you feel in a year.
Tough call. When we sell off one of our "children" we keep the memories (and hopefully lots of photos and video) but the buyer has purchased ownership of a new plaything as well as the right to cherish, abuse or neglect it. Personally I'd enjoy relating everything I could to an obsessed new owner but if it goes the other way you'd better be able to accept it. If you don't think you could, then yes selling to a distant buyer would be preferable. Have a Happy, Healthy, High Mileage New Year Everyone!