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The answer would be to read the Release Notes for the version you're going to install, there are details in there of any required intermediate upgrades or special steps you may need to take. Other than that you can upgrade Zimbra from any previous release to the current release without intermediate upgrades. Always check the Release Notes before any upgrade.
if you look at the release notes for versions there is always instructions for upgrading from previous releases. Like there are special instructions for upgrading from 5.0.2 and eaerlier. If you don't see any caveats I think you can assume that an upgrade from your version is fine.
5.0.9 > 5.0.11 is fine. The installer takes care of things like db schema upgrades (see /opt/zimbra/libexec/scripts).
However coming off a older versions you might want to do a few smaller hops, as we don't test upgrades from every EOL version. So one might go 4.0.5 > 4.5.0 > 4.5.11 > 5.0.11. (Plus we've greatly improved a few certificate quirks on the lower 5.0.x releases that are nice to avoid.)
For 4.5.x to 5.0.x I highly recommend a stop of at least something higher than 4.5.7 as there we're lots of Tomcat & LDAP changes. Of course if you have replicas we suggest going though 4.5.11 as well: LDAP Replicas 4.5.x to 5.0.x - Zimbra :: Wiki
Thanks to all replies.
So officially the answer is, It depends.
Thanks for the tip on the README file, I've been duped
so many times by outdated README's, or worthless ones,
that they become easy to ignore.
(Maybe Zimbra's are an exception?)