1st booking check-in was okay as it was just a single re-position flight. but when I try to check-in my 2nd booking, a 5-segments booking, I get:
I have an 8 segments on single day booking last year and didn't ran into this issue. So, look like I will be visiting the check-in agent every single day to get all my BP.
Departing multiple times from the same airport will also prevent you from doing OLCI. Seeing the agent is fun, they will give you the "you are crazy" look.