There are oodles of ways to move files between Android and your PC. When not using a USB cable, I mostly use Dropbox. But at home I just hook up the USB, select Mass Storage, and the option pops up on the computer to open 2 different folders. The first folder is the internal sdcard, the second is the external sdcard. Just move stuff the same way you would with any other windows folders.
And I know there are at least a few apps that will keep you synced with your Outlook, but I'm not sure about MS Calender.