Okay I finally got my jetting pretty much dialed in. I think what threw was that I was under the assumption that this bike was running lean because before I bought it, my buddy scuffed the piston whilst at the dunes.

Anyhow, now I'm running a 250 main with a 35 pilot and a stock jet needle with the clip in the second position from the top. That last bit threw me, but ended up being the key to my jetting woes.