How can I download music files (MP3) and video files (AVI) to iPod Nano?

I just want to download music files (MP3) and video files (AVI) to my son's iPod Nano and iTunes has all menus grayed out, can't get on Apple support site to upload diagnostics file. Driving me mad - should be simple... Please help!!! Dump of diagnostics below:
Microsoft Windows XP Professional Service Pack 3 (Build 2600)
INTEL_ DG41RQ__
iTunes 11.1.3.8
QuickTime 7.2
FairPlay 2.5.16
Apple Application Support 2.3.6
iPod Updater Library 11.1f5
CD Driver 2.2.3.0
CD Driver DLL 2.1.3.1
Apple Mobile Device 7.0.0.117
Apple Mobile Device Driver 1.64.0.0
Bonjour 3.0.0.10 (333.10)
Gracenote SDK 1.9.6.502
Gracenote MusicID 1.9.6.115
Gracenote Submit 1.9.6.143
Gracenote DSP 1.9.6.45
iTunes Serial Number 0012B9B00CB27BC0
Current user is an administrator.
The current local date and time is 2013-12-22 23:15:54.
iTunes is not running in safe mode.
WebKit accelerated compositing is disabled.
HDCP is not supported.
Core Media is not supported. (16002)
Video Display Information
ATI RADEON XPRESS 200 Series
Intel(R) G41 Express Chipset
**** External Plug-ins Information ****
No external plug-ins installed.
**** Network Connectivity Tests ****
Network Adapter Information
Adapter Name:        {E4F794BB-151F-490C-8AC0-1EDB6DA3718A}
Description:             D-Link DWA-125 Wireless N 150 USB Adapter(rev.A2) - Packet Scheduler Miniport
IP Address:              192.168.5.104
Subnet Mask:          255.255.255.0
Default Gateway:     192.168.5.1
DHCP Enabled:       Yes
DHCP Server:          192.168.5.1
Lease Obtained:      Sun Dec 22 21:35:11 2013
Lease Expires:         Mon Dec 23 21:35:11 2013
DNS Servers:          91.216.105.75
                                216.93.191.228
Active Connection: LAN Connection
Connected:              Yes
Online:                     Yes
Using Modem:         No
Using LAN:              Yes
Using Proxy:            No
Firewall Information
Windows Firewall is on.
iTunes is enabled in Windows Firewall.
Connection attempt to Apple web site was successful.
Connection attempt to browsing iTunes Store was successful.
Connection attempt to purchasing from iTunes Store was successful.
Connection attempt to iPhone activation server was successful.
Connection attempt to firmware update server was unsuccessful.
The network connection timed out.
Connection attempt to Gracenote server was successful.
iTunes has never successfully accessed the iTunes Store.
**** CD/DVD Drive Tests ****
No drivers in LowerFilters.
UpperFilters: GEARAspiWDM (2.2.3.0),
D: LITE-ON DVDRW SHW-160P6S, Rev PRS2
Drive is empty.
**** Device Connectivity Tests ****
iPodService 11.1.3.8 is currently running.
iTunesHelper 11.1.3.8 is currently running.
Apple Mobile Device service 3.3.0.0 is currently running.
Universal Serial Bus Controllers:
Standard Enhanced PCI to USB Host Controller
Standard OpenHCD USB Host Controller
Standard OpenHCD USB Host Controller
Standard OpenHCD USB Host Controller
Standard OpenHCD USB Host Controller
Standard OpenHCD USB Host Controller
Intel(R) 82801G (ICH7 Family) USB Universal Host Controller - 27C8. Device is working properly.
Intel(R) 82801G (ICH7 Family) USB Universal Host Controller - 27C9. Device is working properly.
Intel(R) 82801G (ICH7 Family) USB Universal Host Controller - 27CA. Device is working properly.
Intel(R) 82801G (ICH7 Family) USB Universal Host Controller - 27CB. Device is working properly.
Intel(R) 82801G (ICH7 Family) USB2 Enhanced Host Controller - 27CC. Device is working properly.
FireWire (IEEE 1394) Host Controllers:
Texas Instruments OHCI Compliant IEEE 1394 Host Controller
Connected Device Information:
IPOD (K:\), iPod nano (7th Generation) running firmware version 1.0.2
Serial Number:         DCYK27TGF0GT
Bus Speed:              61440
**** Device Sync Tests ****
No iPod, iPhone, or iPad found.

Hi fkerrin!
In case you haven’t already tried this process before, here is an article for you about syncing media to the iPod:
iTunes: Syncing media content to iPod
http://support.apple.com/kb/ht1351
Thanks for coming to the Apple Support Communities!
Regards,
Braden

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