I could not open your files so I made a fast dirty model just to show you how the "copy with mates" works.
here is a new assembly with the PCB
In the ribbon, go to "Inster Component" in the Assembly tab and choose the first part to place. This will be the pin.
The first mate will be the bottom face of the pin coincident to the top face of the PCB.
The next mate will be a concentric made between any part on the pin and one of the holes in the PCB.
This will be the mate we will use to copy the part with.
After the part is fully mated, exit out of the mate window.
Right click on the part to be copied and select "Copy with Mates"
All of the mates associated with that part will show up. The mates that you want to keep place a check in. For this one, the two faces coincident are the ones that will be the same so place a check in the "repeat" box. Now the box under concentric will be be blue, this is where we will start copying our part.
Left click on a hole the part will copy there. The image does not show my mouse cursor but an image of your mouse should appear with a green check on the right button. click this to accept and then select the next hole.
You can continue left click and right clicking until all the pins are placed where you need.
When finished just exit out of the Copy with Mates menu.