I think had it been a more clear demarcation, like this, Perl 5 would be in much better shape today. Perl 5 has been doing well for a few years now, but it took a while for the Perl 5 developer community to fill the void left by Larry; there just wasn't an acknowledgment that there was a void to fill. Larry didn't die, still kinda paid attention to Perl 5 for a while, but his heart wasn't in it and his attention eventually shifted fully to Perl 6.
Now, the Perl Pumpking (a sort of Benevolent Punching Bag for the Next Release; they do have the ability to decide which patches go in, but usually don't wield it like a dictator) along with the dev community, does their thing...the pumpkin gets passed along every year or three, and things continue. And, Perl 5 is developing nicely in a way that it didn't for about a decade while there was so much uncertainty. The Pumpking existed before Larry left Perl 5, but acted more in a support role (as I understand it), so it seems like it took a while for it to become an acknowledged executive position when Larry faded from view in Perl 5 development.
I think Guido is doing the best thing for Python. If his heart isn't in it, stepping back in a clear way is much more helpful that drifting away and leaving a void of leadership with no one feeling empowered to step up. There are people who are recognized as being contenders for the throne, and there's already a long-standing community process. I think Python will be fine.