[GoodThings2Life]

Let's make this as simple as possible...

Hotmail = Email, Contacts, Calendar, Tasks. You can sync all your contacts to that, and then they'll always be accessible regardless of the PC or device you're using. This includes photos but see the notes below about Zune.

Zune = Music, Pictures, and Videos. That's it. It's also your software point for accessing the Marketplace on the PC. Also, throw all your Caller ID pics in a Pictures folder called Caller ID or something, and they'll sync and organize that way on the phone via Zune. Also, keep in mind that if you link up to Facebook or other social network, contact photos will download and apply automatically with no need to manually assign them. Likewise, if you set the photo via Windows Live Hotmail or GMail, they will sync automatically across devices and platforms.

SkyDrive = Documents. You can forget about using on-phone storage for EXE, BAT, ZIP, and RAR... you can't use them on Windows Phone anyway. However, all those things can be stored on SkyDrive for web-based access on other PC's, so take this time to make the transition now. It's a much more accessible solution than storing them on a card anyway.