Yikes long post... got as far as the car dieing on highway. When you were boosting it you were putting a small charge on your battery and your car would run till that charge was drained , only damage you could have done there was hurt your battery... however i saw you had a wire unhooked from alt.. hook it back up , charge up your battery to full and see if it happens again... Or you can just unhook the battery with the car running and see if it stalls , if it does its due to a faulty alt... or more bad wires.
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