I am backtesting on a separate mt4 installation, which is offline so the version does not get automatically updated. But the "Exporting to Metatrader" help topic says to run the Tickstory Expert Advisor on a LIVE chart, which I assume means it needs to be connected to the server. Do I generate the config file from my real mt4 installation and then just load it into tickstory?
That's correct - if you want to get the settings from your broker, you'll need to run the Tickstory EA on a MT4 instance that is connected to your broker. This will ensure that all the settings such as Lot size are taken from the server.
You can then load the settings into Tickstory and save them as default.