I'd keep my current scooter, Aprilia Scarabeo 200, as the small bike. For a medium sized ride, I'd go with a Burgman 400. And my dream machine would be a fully dressed Electra Glide. That would be my personal heaven.
2009 Aprilia Scarabeo 200 with a large Givi windscreen
I ride it to work every day I can. And some days I shouldn't.