Hi @IronBones!
Depending on how much data you need, or the method of consuming said data, it can be as simple as monitoring inbound dashboard e-mail alerts and reacting to any expired licenses prior to the grace period.
On the other hand, you could run a script that makes the API call getOrganizationLicenses and pull each expirationDate against each licenseKey, comparing them against the current date and alerting on proximity to that expiration date, or parsing the output to a CSV file for review elsewhere. There's a useful three-part guide on the community forums here that details how to use the API with Python.
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