Hi Neo,
I would like to answer your questions,
1, Yes Orange version was working ok
2. Yes Email was queuing on the on premise server, as EOP was refusing to accept connection with the TLS error message.
3. Yes Cloud to On Premise works fine. Cloud to Cloud work fine also.
4. The Hybrid Wizard created the Send Connector for the domain " domain.mail.onmicrosoft.com " messages sent to cloud through this connector just sit in the Delivery queue because of the error message. Other internet mail is relayed via the Internet Mail Send Connector ok.
I am using the EOP, I have run the HCW several times, and I have deleted the connectors then re-run the HCW and it has successfully recreated the connectors again.
Ian