So, at what point to you move a script to the latest, greatest version of Perl?

It depends. Two criteria are certainly the ones you mentioned.  And yes, I generally do have quite a number of Perl versions installed on my machines (7 on this box, for example, reaching back to 5.8.4).

Other criteria are

• When I've got myself a new box (hardware), or have had some reason to wipe/upgrade my entire OS, I (re-)evaluate whether getting any "ancient" versions of Perl set up again on the new system would be more trouble than getting all app's respective module dependencies built for a new version of Perl, finally.
• When I have some idle time, I sometimes simply invest it to upgrade XS modules for no particular reason other than getting them upgraded, and eventually being able to drop ancient versions of Perl.

All in all, this migration process is kind of natural and "automatic", in that the longer some Perl release isn't superseded by another bugfix release, the more upgraded modules I happen to have for that release...  New projects are generally started with the most recent release — which creates the "need" in the above outlined upgrade-as-needed approach, for the particular modules used in that project...

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