IMac – Messages app gives an upgrade notice but never finishes

So I ended up just starting up from the recovery partition and reinstalling OS X.

The Reinstall Mac OS X option is like upgrading from 10.7 to 10.8: it could just as well be called something like repair OS X. I only had to reinstall Java, replace Apache configuration files, and so on.

Everything seems to be working now. I can access localhost again, and my app is running Sinatra on Thin as it was before. Thanks to bmike, I did a bit of searching on why my loopback was unreachable and came across this article. I moved my old hosts file (/etc/hosts) to hosts.old and made a new one in its place that simply contained:

##
# Host Database
#
# localhost is used to configure the loopback interface
# when the system is booting. Do not change this entry.
##
127.0.0.1           localhost
255.255.255.255     broadcasthost
::1                 localhost
fe80::1%lo0         localhost

Then, I ran dscacheutil -flushcache and rebooted my computer*. After that, things appear to be working normally again. I can only guess that something weird happened with my old hosts file. I also took JakeGould's advice and blew away ruby 2.0.0 (I still had ruby 1.8.7--you cannot uninstall ruby entirely on a mac, since it uses ruby for other things) and rvm and reinstalled those; but I'm not sure that had anything to do with my success, as I still had the same issues until I followed the steps outlined above.

Note: the above hosts file contains virtually the same thing that I say my hosts file contained before (see original question); however, there were other things in my original hosts file that I did not share in my question (I just shared what I thought was the relevant part), so perhaps something there got borked when I upgraded--I wish I knew for sure.

*Rebooting is probably not necessary. I actually had this problem after setting up a new user from a backup drive on my machine at work (which is running Mountain Lion) and (just today) followed the same steps above (minus blowing away ruby and rebooting the machine), and it worked. This leads me to believe that the heart of the issue was a borked /etc/hosts file.