Where I'm probably the worlds biggest DR650 fan (I've owned a 91, 97 and a 2009) I've also owned a 2008 XT250 that had all the power I needed for anything I wanted to do, and I took that little girl places I NEVER would have thought to take any of my DR's.
If it hadn't suffered from Yamahas cost cutting for suspension and finish, I'd have loved to have kept her.
Point = I don't think there's anything that little bike couldn't have done, (solo riding) except survive another Pa. Winter, without rusting/rotting away.
F.W.I.W. if Suzuki ever brings a street legal (has to be from the factory in Pa.) DRZ250S here...I'll be on it like flies on shit regardless of my financial state. I long for a mini DR650 in the worse way. ( the DR200 just isn't quite "enough" bike)
The magic of a small bike is the ease in which you can get it out of jams, the flick-ability on tight back roads and tight trails where too much bike can become a chore and the lack of its ability to pound you into the ground like a tent stake. (although, it can still happen if you try really hard)
I think the only place a "big bike" really shines, is on roads with heavy/fast (75mph+) traffic, and who wants to ride there?