The TE250 has been street legal since '06. Curb weight (everything except gas) on the '06 was 244 lbs. I think it was like 33 hp at the wheel. The TE250 is damn close to the perfect woods weapon that's street legal to boot already, 310 would be even better. However, neither will be the street bike that the WR-R is.
Husky maintenance isn't bad (valve checks are very easy), would be more than the Yam though. Tranny ratios are SUPER close, maybe they will change it on the '09. No dealer nearby is pretty much a non-issue, parts are easily available mail order.
I stepped down from an '06 TE250 to my modded '07 KLX250. TE was too much bike for my riding, too tall and short geared. There's hardly any off road riding in my area. My right arm/shoulder are less than 50% strength/range of motion so I just needed a more mellow bike.
I do miss the Husky though