I considered the newer GT versions of the People and I decided in the end to get the Downtown instead. After owning my (non-GT) People 250, with it's tons of underseat storage + topbox, I just couldn't go for the GT version (which essentially has just a small glovebox under the seat).
I originally planned on selling the People 250 (as that was the justification for getting the Downtown, but after changing the tires, it addressed my biggest complaint being poor handling (had head-shake and a bit of top-heavy feel to it). With new City Grips front and back, all of that is gone, and it rides more like a motorcycle.
In terms of other maintainance, in addition to tires and normal oil change/lube/air filter, I changed the belt, brakes, and that's about it.
I'd think a 250 be perfect for riding 2-up, especially around eastern Ohio backroads. The HD200, if I'm not mistaken, although from what I hear it's an excellent ride, it won't give you much more power than you already have on the 200i.
For reliability and servicing, from my experience owning both Kymco and SYM while in Taiwan, they are similar. What steered me towards Kymco when I moved back to the states was dealer network and parts availability.
Hope that helps