I believe that the new computers could handle multiple things plugged in at the same time. Do you have enough USB ports? If not then maybe get a USB hub to have more ports available for use. Best Buy has USB hubs for purchase as well. You will need iTunes installed on your computer in order to transfer your music to your iPod. Maybe first rip the CDs onto your storage device and then sort your music library in iTunes? As an alternative, if you have iPod touch you can always add streaming service to your device, such as Spotify or Amazon Music Unlimited.