Perl is usually very backwards compatible - some say too much - and very outspoken in reporting changes and deprecations.
Changes mostly affect exotic features or unsuccessful feature experiments.
I'd say the best strategy is to use perlbrew and install various versions to run your code. Check the logs for errors and warnings.
And try establishing automated tests to assure that your application "works" as intended.
You can either gradually increment the version, or just do a binary version search till it breaks.
My intuition tells me that you'll rather have problems with CPAN modules in your dependency chain or third party components of your application. (I once had an application which suffered from a subtle break after MySQL was upgraded)
But that mostly depends on the quality of your code.
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