Board Thread:Theories and Speculation/@comment-36157725-20180816213118/@comment-5407586-20180817065507

Madara would've chosen Sasuke over Obito because the former is cool-headed, has good analytical skills and awakened the same Choku Tomoe as him. I believe that the last point is what made Madara decide, since he was searching for someone to take his place. Obito was the best he could find during his lifetime. Ironically, Madara would've never met Sasuke before his "real" death, due to the two of them being trasmigrants of Indra.