I'd go with either Ubuntu or Fedora / Centos.
Ubuntu has better support for ndiswrapper which is frequently used to get wireless networking functioning. WEP is supported, WPA will require the WPA supplicant add-on package.
The latest version of Open Office's Evolution email client, a clone for Microsoft Office, now works with Outlook / Exchange calendaring. This was a major reason for me not considering Linux on the desktop in the past.
There are a lot of Linux MP3 players.
USB sticks are auto detected and a link should automatically pop up on your desktop.
I'm not sure about the rest. Practice on a test system before going fully Linux.