I use an rsync command in a .bat file on Cygwin. It's reliable and not too hard to set up.
Start at cygwin.com
, and be sure to add the rsync and OpenSSH packages when you install. Note that you do not need an rsync server (rsyncd) running on the Linux machine; just an ssh server will work. You do need to have rsync installed on the Linux machine.
Your command should be something like:
rsync -av --progress -e ssh /cygdrive/c/ email@example.com
You could also try this prepackaged version of rsync:
Though I haven't used it myself, Unison seems to be pretty popular: