Well hooray for taking the city!
It seems like it was probably a bad idea for them to retreat, don't you think? Unless there are a bunch of reinforcements coming from other CUDDLE teams.
I think the plan to advance on Kiwi Town and cut the road is good. However, 3 workers should be able to road the desert tile SW of their mini-stack, so if they think of it they should still be able to reinforce Kiwi Town in 1 turn. Of course if they do that their workers would be vulnerable to attack.
I agree that we don't need to use the artist on Kalin's Burgers. I assume you meant you wanted to settle 2E of Bill's position, not Rooster's.

I'm not sure about the exact location, the site 2S1E of Bill seems better to me. Also, for the great Artist bomb, you don't need to actually spend a turn at 100% culture, you just need to make sure that you're at 100% culture when you use the artist for the bomb. So it's kind of stupid it works that way but it's free so we should do it.
I noticed that Blake's whip unhappiness expires next turn. Should we whip something there soon? Also, Sirian has a Scientist hired. Don't we want to try to keep a pure pool of Engineer points there?