I tend to fall in the "if it ain't broke don't fix it" category, with the exception of critical updates.
But I just realized that I'm running Perl v5.10.1, that had an EOL in 2009! That might be a bit much.
I really need at least 5.14.4 to use some features that I want, but I'm nervous about updating. I have several hosted clients that use Perl (even if they don't know it), and some of them haven't been updated in YEARS! I worry about updating Perl and then some of their modules stop working.
So what do you guys think... leave well enough alone and forget about those nifty little features (like s///r), update to 5.14.4 and hope for the best, or go all in and update to 5.28.2?