As part of our evaluation I would need to stop running my Windows based Jira installed with Evaluation License and install and run new Jira instance on OS-X. Is it possible to achieve this using the same Evaluation License, please? Won't I get locked out not able to run neither of those at the end?
No it is not possible as every server evaluate different Evaluation License.
If possible then migrate your JIRA into another system using below link
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