I like his music but is he really a mountain to climb?
Yep. One of the first [and most prolific] singer-songwriters. Invented his own sound. Produced [after spliiting with his original label] his own records. Used strings [including some pizzacotto] on his records. Played everything from rockabillyto ballads to straight rock to blues. Did all of it well. Did all of it in less than four years.