So from the screen shots provided, it is not possible to determine if you are handling the inbound leg of the call correctly. In inbound routes, you need to direct the inbound call to the Set CallerID destination you created which does the CID modification, which in turn directs to ext 400 then to the exterior number. I don't think you want intra-company checked on your outbound route, but your own testing will determine for sure.
I had initially missed the fact that you are running PIAF, which is a fork of FreePBX and not really supported here. Your paid support option in this case would be a best effort only, with no certainty that your system would behave in the same manor as the official FreePBX distro. Rather surprised they directed you here for support.