IMessage keeps popping up

The serial number may be an issue. When MacOSX thinks it is running on dodgy (i.e. non-Apple) hardware it usually has far more severe problems. There's no lockdown of an installation of MacOSX to a particular Mac, i.e. no DRM with keys and mandated validation with the vendor as with Windows. Apple cares most about people buying hardware, so the only "piracy" of MacOSX that they interfere with in code is running it on non-Apple hardware. But since my first version of this, I have been pointed at http://www.apple.com/support/icloud/contact/ by someone too polite to call m stupid in public, and that has strong sign of iCloud/SN linkage.

There's nowhere near enough info in the question to provide a sure answer to your problem, but there are clues pointing to possible issues. To figure it out, you should start by shutting off Little Snitch and the built-in firewall. You probably will want them back on eventually, but they should be off while you are trying to get complex services working to assure that they are not able to cause secondary blockage. And because you mentioned it, you get a rant: NEVER add entries to /private/etc/hosts on a modern MacOSX except for the 4 that the system needs for proper loopback initialization at boot time: IPv4 localhost and broadcasthost plus 2 forms of IPv6 localhost. if you have anything else in there, you should remove it. Once you've eliminated the possibility that your system config is explicitly blocking communication, you can look to the outside. All of those services include mechanisms to set up direct connections between 2 machines that may have IP addresses which are temporary and/or may be behind a NAT gateway that translates their traffic between a public and private (unroutable) address. Unfortunately, it is also possible for external network devices like routers and firewalls anywhere between the two ends to thwart those mechanisms. If you are behind a tight firewall, you will have trouble. If you are behind 2 layers of NAT, you will have trouble. Knowing what trouble you have isn't going to be discernible with toys like the Little Snitch network monitor, since the error you're getting probably involves just a handful of packets rather than any ongoing flow. To know what's happening you'd need to use a tool like tcpdump or wireshark and have an understanding of what you're looking at and looking for.

Try this.

Uncheck "Speak an announcement".