I thought I'd try Windows Live Writer. It won't work with Windows 2000, which I use because I despise product activation. (I do a LOT of PC setup and tear-down, with a lot of OS re-installs.) Bummer.
Then I read about Windows Live Writer Portable. It actually works -- under Windows XP. Under Win2K it crashes. I'm betting it is using DotNet 3, which is a no-go on Win2K. I do have GDI+ installed on my Win2K, so it isn't that.
Or maybe it has a dependency on IE7? Good luck getting THAT to run in Win2k!