In this specific case, I was able to update the template, control Live, and otherwise use the iPad with no problem. Ableton Live, however, would not update the template or send control signals. The root of the issue was that any communication from the iPad to a host would reach it's destination, but any communication from the host would not reach the iPad. One sure way to identify if this is an issue for you is to go into your wireless settings and renew your DHCP lease. Note the IP address you were assigned. Next go into TouchOSC and check your Local IP address in OSC. If they are different then it is certain that you have bad connection information cached on your device - TouchOSC reads the cached network settings.
If you are having this same problem, give this a try. It will work the same whether you're on an iPad, iPod Touch, or iPhone. Go into General > Reset > Reset Network Settings. You will only be resetting connections, not the device. It is not dependent on OS X or Windows, if this problem applies to you the device is at fault.
LiveControl is just. so. awesome. I was almost late for work this morning because I stayed up late geeking out with this thing!
