My 08 is completely stock aside from a painted windshield and fender chop, and I have never experienced any sort of wobble on my bike. I take my hands off the bars fairly frequently to stretch my arms and shoulders. It's usually at speeds around 50 on my way home, but I have done it as low as the 20s and as high as the 80s. Never any sort of wobble.
With all the stuff you have done to your bike, it may be a very slight misalignment somewhere. The rear tire sounds like the best starting place based on your tail bag experience. Good luck and keep us informed as usual!
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2008 Green 250R
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