What type of e-mail account do you have? It seems to defeat the purpose anymore to sync e-mail to a device through a cable. If you have to be in front of the computer, you can just check your e-mail there.
I mean what type of e-mail account is it? POP or IMAP? If it is IMAP, you can set up the e-mail account directly on your iTouch, and just use wireless to get the mail directly from your host.
I noticed you said "contacts and calendar" without mentioning mail. When your iPod Touch has web access, you can login to your Live account through its browser and see the same contacts and calendar data that WLM would see (when "signing in"). But if you want to download the contacts and calendar so you can "work offline", I'm just not familiar with the Apple products. Perhaps there's an app for that.
My Computer
Computer type
PC/Desktop
Computer Manufacturer/Model Number
OQO 2+
OS
Windows 8 Pro w/MC 32-bit
CPU
Intel Atom 1.86 GHz
Motherboard
OQO 2+
Memory
2 GB
Graphics Card(s)
Intel GMA 500
Sound Card
IDT
Monitor(s) Displays
LCD
Screen Resolution
800 x 480 (portable) 1280 x 1024 (docked)
Hard Drives
64 GB SSD
PSU
9 Ah Battery (portable) or OQO Brick (docked)
Case
Shirt Pocket Sized
Cooling
Tiny Fan
Keyboard
Slide out (portable) DiNovo Edge (docked)
Mouse
Eraser head (portable) Logitech Bluetooth (docked)