1986 XR 600 Mods???

Well, I finally got my 86 XR 600 running decent and its ok but I want more power, I know the valves need a regrind and the rings are a little shot. I think it is pretty much stock other than the Supertrapp exhaust and the 14/45 gearing (I don't know what gearing is stock) I was thinking about doing an 11:1 wiseco, bored out to whatever it needs to be cleaned up, or milling .01 or .02 off the stock head with a 9:1 Honda piston or Wiseco. I was also going to clean up the ports on the stock head and put a hot cams cam in it. I have been hearing about these things having tranny problems and it makes me a little nervous. Should I just pawn this thing off and get a newer one to play with and invest money in? I like this bike but don't want to ever split the cases. 2nd gear seems a little hard to shift under power, is this a sign that its getting ready to go? I was thinking maybe it was my clutch. Any suggestions would be greatly appreciated.

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