IE bookmarks?
Chrome browser or Firefox browser will sync book marks without you having to do anything.
Make these settings in Chrome, then have it import all your IE bookmarks.
On the phone go to Settings / Accounts and Sync, tap your google account and make sure Sync Internet is checked.
(also calendar, contacts, gmail, and what ever else you want).
There is similar capability with FireFox, but the above is built right into your phone. Don't expect Microsoft to make it
easy for you. The best experience on an android phone is to do as much as you can with free google services.
Sync your outlook contacts with Google Contacts, and then they will automatically sync with your phone. There are
bi-directional tools for that available for outlook.
For pictures, there are lots of options, Picasa Web Albums can automatically sync with your phone, Dropbox allows
bidirectional syncing between phone and computer, the phone comes with Flickr app, and there are a couple dozen more
in the app store.
With any file manager, such as ES File Explorer you can drag and drop images or music to or from any windows share
over the wifi network.
Any sync method that involves a USB cable is up the wrong tree barking. (And its long since time to
get rid of Internet Explorer).