I like having the chance to play in a show multiple times.  I feel like I can dive deeper into the show, and apply the additional life experience (including the previous run of the show) to the new run.

I did Big River when I was 11 or 12 (I was one of the boys) and then did it again when I was 16 as the King.  Knowing the show really helped me to play up the part, but also helped me see how I had grown as an actor/performer.

I did Joseph and the Amazing Technicolor Dreamcoat in high school, and then did it ten years later in community theatre.  Both times I was cast as Judah, which I think is a testament to my ability to sing the part... and it was a great opportunity to show myself how I've matured.

A fun show is still fun the second time.  I can't speak to it on the third iteration, however.  And I have yet to direct a show that I had previously acted in.