Does this support running X over SSH? The biggest drawback for me with Windows boxes was always a lack of X support for applications I want to run on remote servers.
Yes. From the stock bash prompt, run "startxwin". With the resulting xterm, you can launch any X apps within Cygwin, or you can SSH in (with appropriate flags and xauth config, etc.) and blow back X apps from the remote Unix box. It's really nice.