This really seems like the 1. scenario to me.
There is this line:
[2020-03-09 11:10:12.271 -04:00][Trace] - {PayloadSenderV2} Waiting for data to send... FlushInterval: 10s - so time is [2020-03-09 11:10:12.271, and the timespan of the last line is 2020-03-09 11:10:20.205 -04:00 - so if the process does not live 0:0:2:067 (~2 sec and a little bit) longer then the agent won't even try to send the data.