Thanks for all the help!
I guess I can definitely cross performance off my list of concerns.
No question that scooters are just inherently geared towards carrying things. I seem to recall someone saying they're like two wheeled pickup trucks, which is apt. I'm sure I could fit quite a lot of beer in the top box, under the seat, and by my legs on a People 250.
On the motorcycle I'm considering in particular, it sounds especially sounds like it takes some effort to get it ready for all the bags. For me, at this point, that just sounds more fun than discouraging though.
Also agreed that for cities / stop and go traffic, scooters are an obvious choice. But less of a concern for me, living in the middle of nowhere -- I'm more concerned with the 40-100 mile trip to get to the city than how it is driving around it.
Also, that motorcycle ergonomics website is amazing, although I'm not totally sure how to interpret the information.
http://cycle-ergo.com/According to it, it seems like the small cruisers and the People 250 have you in very similar positions though?