I have owned two DR650SE, and they are dependable, cheap to keep, lower tech tractors of a dual-sport and a bit heavy. Better on the highway and for riding two up, etc. I have a 06 KLX250s, and it is a bunch better in the woods, but is down on top end speed when doing short hauls in heavy freeway traffic (scary). The WR250 has more juice, but a 250 will be short of the torque of a larger engine. You alone can decide.
Tell me Doctor, where are we going this time.......