Sim goes in with contacts down (towards PCB).
With the virtual COM driver normally you just delete the driver and allow windows to find the WHQ driver. You may have to show hidden devices first or see if it is listed as unknown.
For testing I would start with the RSSI example. Add some code to the uart module so that you can see what is going on. I added some to send_cmd (both functions) and wait_for_resp. You should see the result of the +CPIN? as READY which shows the SIM is ok.