@Tr00g33k - The uploading issue can sometimes be due to a bad Ruby package. Try updating the ruby packages to the latest development packages and see if that helps. In terms of it not connecting back - make sure the executable has exited correctly on the other system when reconnecting, and that you're not running any other instances of Metasploit on the current PC (i.e., by doing a "ps -a" and looking for any related ruby processes). Also, make sure no firewall that could be getting in the way is.
@lil-hard - All I can say is that without the proper port forwarding or an external server, you won't be able to do it externally. And you can't do proper port forwarding without router access. Either ask your neighbour for his router password, or rent an external server to do it.