Any insights as to why I am having issues with OS 10.9 and not 10.15? I
understand both are supported by LMS 8.2.0. Thank you!

Your Mac's SSL libraries are outdated. See the following link for instructions how to update them:

https://forums.slimdevices.com/showthread.php?109738-Error-Can-t-connect-to-remote-server-to-retrieve%85&p=925539&viewfull=1#post925539
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