Clutch???
 

I seem to frequently have problems shifting into second gear when i'm shifting under a power situation. Does this mean that my clutch is dead, or is it something more, like my tranny?

Sounds like 2 nd gear synchronizors. You'll probably get better advice in another forum though, depending on your exact application.: Classic, 5.0, or Modular.

Rev

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'66 Coupe, 306, 300 HP, C-4, 13.97 e.t., 100.3 mph
1/4 mi.