Sportcity 250 rider here and I love it as well.
My only issue is the market for windscreens, either to short or to tall and being a bit closer to where the screen would be compared to maxi scooters it is a factor. Oh and it doesnt look like a Triumph Bonneville which is sexy as can be but that is a different subject.
My gut tells me resale isnt going to be great because in all honesty there are a ton of the SC 08-09 models around.
Is it possible to do multi-state tour on it? yes. I havent yet but people here have.