Error 2:
[2020-07-09T15:58:54,431][ERROR][logstash.licensechecker.licensereader] Unable to retrieve license information from license server {:message=>"Unrecognized SSL message, plaintext connection?"
Could you post your Logstash config so we can form a better idea of what you are doing?
I had the license checker error as well, albeit not with SSL, and the problem was I misconfigured the xpack monitoring in Logstash in the logstash.yaml...
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