My local riding is nothing but ridiculous hills out of corners, and Hancock, NY takes it to another level. The kid (nephew) will spank most of us (Bs and Cs) with his GG125, and did great in Hancock last month. You just have to ride it different. Now in your case being a young fast guy riding with guys of the same ability on faster bikes, I can see that being a disadvantage. For skid, and guys like him (and many of us), it could be an advantage.
I really hope the GG 250F is a good bike and not a grenade when it comes out, with minimal teething problems. I really like the GG chassis and 250F power, and would likely buy one in its second year.
Skid,
If you don't have a G2 throttle on that 300 you should try one with the #400 cam. It will really take the edge off. I even put one on my Hypermotard, which has viscious off idle torque that makes it tiring in traffic sometimes, and its MUCH smoother.