Problem synching calendar to 5gen iPod nano (Vista Home Premium SP2)

My iPod 5gen nano will not sync my Outlook 2010 calendar, and thus my To Do Lists, which I use for college. I am using iTunes 10.1.0.54 on Vista SP2, I get error messages on some occasions, (one stating something about logging in or out of Windows?) and crashes on others. I really need my calendar to sync.

You posted to the wrong area of discussions. This is the 5th Generation iPod group (the video full sized iPods that were released previous to the "Classic" models). If you are asking a Nano question, you want to post to this area...
http://discussions.apple.com/category.jspa?categoryID=265
Regards,
Patrick

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Microsoft Windows Vista Home Premium Edition Service Pack 2 (Build 6002)
Sony Corporation VGN-NS20E_P
iTunes 10.6.1.7
QuickTime 7.7.1
FairPlay 1.14.37
Apple Application Support 2.1.7
iPod Updater Library 10.0d2
CD Driver 2.2.0.1
CD Driver DLL 2.1.1.1
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Apple Mobile Device Driver 1.59.0.0
Bonjour 3.0.0.10 (333.10)
Gracenote SDK 1.9.5.502
Gracenote MusicID 1.9.5.115
Gracenote Submit 1.9.5.143
Gracenote DSP 1.9.5.45
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WebKit accelerated compositing is enabled.
HDCP is not supported.
Core Media is supported.
Video Display Information
Intel Corporation, Mobile Intel(R) 4 Series Express Chipset Family
Intel Corporation, Mobile Intel(R) 4 Series Express Chipset Family
**** External Plug-ins Information ****
No external plug-ins installed.
**** Network Connectivity Tests ****
Network Adapter Information
Adapter Name: {78DA402D-66EE-4084-9D5E-8A010E0B8437}
Description: Atheros AR928x Wireless Network Adapter
IP Address: 192.168.2.8
Subnet Mask: 255.255.255.0
Default Gateway: 192.168.2.1
DHCP Enabled: Yes
DHCP Server: 192.168.2.1
Lease Obtained: Sat May 26 19:10:42 2012
Lease Expires: Sat May 26 19:10:41 2012
DNS Servers: 192.168.2.1
Adapter Name: {C1458549-CA0B-4A3B-8F8E-9259653AA0DD}
Description: Marvell Yukon 88E8055 PCI-E Gigabit Ethernet Controller
IP Address: 0.0.0.0
Subnet Mask: 0.0.0.0
Default Gateway: 0.0.0.0
DHCP Enabled: Yes
DHCP Server:
Lease Obtained: Thu Jan 01 00:00:00 1970
Lease Expires: Thu Jan 01 00:00:00 1970
DNS Servers:
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 NOT 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 unsuccessful.
The network connection timed out.
Connection attempt to firmware update server was successful.
Connection attempt to Gracenote server was successful.
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**** Device Connectivity Tests ****
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iTunesHelper 10.6.1.7 is currently running.
Apple Mobile Device service 3.3.0.0 is currently running.
Universal Serial Bus Controllers:
Intel(R) ICH9 Family USB Universal Host Controller - 2934. Device is working properly.
Intel(R) ICH9 Family USB Universal Host Controller - 2935. Device is working properly.
Intel(R) ICH9 Family USB Universal Host Controller - 2936. Device is working properly.
Intel(R) ICH9 Family USB Universal Host Controller - 2937. Device is working properly.
Intel(R) ICH9 Family USB Universal Host Controller - 2938. Device is working properly.
Intel(R) ICH9 Family USB Universal Host Controller - 2939. Device is working properly.
Intel(R) ICH9 Family USB2 Enhanced Host Controller - 293A. Device is working properly.
Intel(R) ICH9 Family USB2 Enhanced Host Controller - 293C. Device is working properly.
FireWire (IEEE 1394) Host Controllers:
RICOH OHCI Compliant IEEE 1394 Host Controller. Device is working properly.
Connected Device Information:
JULES'S IPO, iPod nano (4th Generation) running firmware version 1.0.4
Serial Number: YM839W553QU
Bus Speed: 61440
Most Recent Devices Not Currently Connected:
iPhone 4S running firmware version 5.0.1
Serial Number: DNWH3R84DTD2
**** Device Sync Tests ****
No iPod, iPhone, or iPad found.

Hello, VvioletT.
Thank you for visiting Apple Support Communities.
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iOS: Troubleshooting USB-related alerts when syncing
http://support.apple.com/kb/TS5254
Resolve issues between iTunes and security software
http://support.apple.com/kb/ts3125
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Problem synching calendar to 5gen iPod nano (Vista Home Premium SP2)

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