Hi, @net1994
Thank you for posting in Microsoft Q&A forum.
We may use File system compliance items to detect the file "thisfont.otf" like you used in software inventory, you may refer to the link for detailed steps:
https://sccmdiet.wordpress.com/2014/09/10/sccm-2012-configuration-items-configuration-baselines-compliance-settings-part-4/
(Please note: Information posted in the given link is hosted by a third party. Microsoft does not guarantee the accuracy and effectiveness of information.)
And you need to create two Configuration Items and Configuration Baselines because the font file could exist in different path as you descripted.
%USERPROFILE% can be used in the path, for your reference:
https://learn.microsoft.com/en-us/mem/configmgr/compliance/deploy-use/create-custom-configuration-items-for-windows-desktop-and-server-computers-managed-with-the-client#bkmk_file
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