It's all going to be one series circuit whichever way you do it:

#1. Hot -> 50' #12 -> 50' #14 -> Tool -> 50' #14 -> 50' #12 -> Neutral.

#2. Hot -> 50' #14 -> 50' #12 -> Tool -> 50' #12 -> 50' #14 -> Neutral.

Either way you have 100 ft. of #14 plus 100 ft. of #12 conductor in the circuit, so the resistance of the extension cords will be the same.