Just my 2 cents, I'm new here and have to start contributing somewhere! I own both a '99 Yamaha WR400f dual sport conversion and a '14 Yamaha WR250R factory dual sport. The power of the 400 is intoxicating on such a light bike (for its time anyway), and just all out fun anywhere. But the 250 feels much better on the street, while not sacrificing much off-road (other than power). Around town and offroad the 250 is great, the only time it feels any pain is on long stretches of uphill highway or when fighting a headwind. I even ride 2up with my girlfriend (I'm 185lbs, she is ~125) on and offroad and it handles the weight just fine, even riding around at Dumont Dunes with her on the back, with just a knobby tire. I've ridden a couple KTM 530's and was very impressed offroad, but on-road was just not very fun at all for me. The bike felt unstable and just overall uncomfortable. Similar to my WR400, but the 400's weight helped it feel a bit more planted on the pavement. I tried a DRZ400 as well but the performance was just sub-par all the way around.