In order to get the "Random City" tool to run (and probably some other tools) you need to install Microsoft .net Framework 3.5 Service Pack 1 into your CrossOver bottle. If this tool isn't installed you get a non-useful error when you start the tool (you'd never guess what this error was without more information).
The error while installing the .Net framework is;
"calibri_0.ttf" cannot be opened because the developer cannot be verified.
But despite the error, the "Random City" generator now runs.