Anyone know if it's possible to make osquery work where the logger sends to the local filesystem?

Yes, absolutely. You are probably sending a config from the TLS server that is overriding

logger_plugin

.

cool. that makes sense. I am using kolide. I will need to figure out how I change its configuration so that it does not send the override. If you happen to know how, please point me in the right direction. thanks

That did the trick. Thank you!