I mean I already have rsa keys setup in my /home/username/.ssh/id_rsa and I can successfully make the ssh connection without entering any password. Does specifying the file with the -i option change the behavior any more than it already is?

Also, is there any place to put the commands that will guarantee the network has already been loaded on startup? Does rc.local already guarantee that? I thought that my be an issue because the ssh commands won't work if there is no network setup already.