If I may suggest this, since you seem to be contemplating when to do the upgrade, to install a temporary version of the current ZC 1.5.5 beta to at least see that it works on your particular configuration as is... If there are issues, report them to the
applicable FEEDBACK ON BETA of ZC 155 thread. This will also tell you what changes you might need to make to support ZC 1.5.5. Appears that you have ZC 1.5.4 working as a temporary site, which is good news, so hopefully not much is needed for ZC 1.5.5 from there.
And yes I know this is a bit of a dig/sarcasm: Looks like have waited nearly four years already what's another month?
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