Route harness and hoses through Transom

[joe7670]

I'm getting ready to route my harness and hoses through the transom. Engine is on a bracket with 24' setback. I bought a fitting that goes into the transom onto which a plastic harness cover screws into(don't know what that harness cover is really called but local supplier recommended it).

I was told that the plastic harness cover goes right into the motor.

Question is should I be routing the hydraulic steering hoses through another hole in the transom or everything through the same hole?
Same hole would require that I poke a hole in that plastic harness cover. Any issues with making that hole?

Also, should the primer bulb be placed after the transom and close to the motor or in the transom?