On the second example , the OBS is working anti directional , if CDI is on the left go to the right to intercept the radial , if CDI is on the right , take a heading to the left to intercept. Outbound means inbound , Inbound means Outbound
Why it is anti directional ? Well divide your Rose into 2 quandrants , put a horizontal line in the middle like if it was the equator .
If your heading coincides to be in the upper part of the OBS ,then your OBS is Directional : CDI left , fly left etc.. Outbound means Outbound etc..
If your Heading happens to be on the lower part , OBS is anti directional.
So it s good practice to reverse the selection 180 degrees . In your second example , CDI should be set to 270 radial. Then it will provide proper information , Outbound when it is true and Fly right to intercept