1. You can cascade or tile windows, or manually resize them so they fit.
It's not clear which application you're talking about, though. If the
windows you want to see at the same time are listed on the Windows taskbar
(usually at the bottom of your screen), click one, then Ctrl+click each
additional window you want onscreen at the same time, then right-click any
one of them and choose one of the Tile options.
2. Contacts, as well as all other Outlook items, are stored in a .pst file.
So, that's what you'd copy (you need to close Outlook to copy the .pst
file). To find out where the .pst file resides, right-click the top level
folder in Outlook (Personal Folders or Outlook Today, depending on which
version you have) and choose Properties... - General tab. Click the Advanced
button. The exact name & location of your .pst file is shown under Filename.