If you need them, you might consider using the Cygwin(64) version of Emacs. The "w-32" version gives best of both worlds, as it does not need an X server. Be sure to start it with a shortcut so it finds $HOME etc.:

  C:\cygwin64\bin\run.exe /usr/bin/bash.exe -l -c emacs-w32.exe

I'm currently a Windows Emacs user. I'm curious, which plugins in particular gave you trouble?

Ideally I wanted to set up an Emacs environment for Python development. I tried to install the plugins mentioned on this page:

http://www.emacswiki.org/emacs/PythonProgrammingInEmacs

Couln't get flymake and pyflakes to work. pymacs was a non-starter so I couln't use ropemacs.

I also tried CEDET, but that was an epic fail.

I use Cygwin emacs in the terminal (mintty). The experience I get from this is very close to Linux (emacs-nox in rxvt).