Not sure if you ever got help on this or not, but the information on setting this up is pretty bad. Almost every How-To I have seen on this subject leaves out a step or two. Welcome to the world of Open Source
I have mine set up similarly, and the input/control of Ableton works, but the data does not update on the screen. I'm still digging hard to figure out why.
Most people I have read have found a few things in your situation:
Windows Firewall - I have had issues with this occasionally, so disable it, just in case
-Usually this will result in TouchOSC not seeing your LiveControl instance under "Found Hosts", in your OSC Connection configuration
It looks like your Ableton Live instance is seeing your TouchOSC server, based on your screenshot. So the problem is likely your TouchOSC instance talking to your iPad... but I'm guessing here
If you see your LiveControl host listed in "found hosts" that's good! At this point, the only other thing I would think it would be is the PORTS, which I have seen conflicting information on. Mine defaulted to 5000/5001 incoming/outgoing, and it WORKS as a controller.
I actually cheated with money and bought touchAble, and it worked 100% out of the box. It was more complicated to configure, and uses 3 separate MIDI channels in its configuration. But it worked both-ways for me, so I have been using it. However, Interface-wise, I prefer LiveControl, and still want to make it work. If I could only overcome the two-way communication issue, it would be great!
Good luck!