I like using Windows Server 2008 as my primary workstation. However, Windows live Writer (WLW) wouldn't allow installation onto 64-bit OS and that includes Windows Server 2008. However, there is an alternative to install WLW onto Windows Server 2008.
  1. Install the Technical Preview of Live Writer
  2. Install the official WLW onto a Windows XP/Vista machine
  3. Copy & overwrite the WLW folder from the XP/Vista machine to Server 2008 (C:\Program Files (x86)\Windows Live\Writer)