The Crowd upgrade process for us has been very reliable - have been using Crowd for 5-6 years and can’t think of one time the upgrade has failed (disclaimer: personal experience only, your mileage may vary etc etc).
backing up crowd before an upgrade is pretty straight forward either using the XML option Ann mentioned, or a DB and file system backup. Rolling back is then pretty painless.
in terms of benefits of 3.x over 2.x, it’s always good to keep relatively up to date as the more distance between upgrades the riskier they can get, security updates (unsure if there’s any CVEs in the version you’re on), but in terms of features a recent version now has a great audit log functionality (with a much more useful audit log search than Jira and Confluence) and a big help for us (but possibly not even noticed by some), whenever a drop down list of directories is displayed, they’re now sorted alphabetically! With 15 directories, this is a big help for us. There was a change (possibly between 2.x and 3.x) where the UI no longer uses the REST API for its own calls instead using its own background access which for us has given a nice speed improvement for administration.
In summary, I’d vote yes.
CCM
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