I am having the same problem with version 7.0.77, it will not automatically update upon loading despite that the settings are set to update as soon as i have internet connection.
This seems to be a different issue. The issue from above was related to an error in Weather Underground's weather data feed. That issue has been resolved, and still is as far as I know.
everytime I start my PC and WW loads to the systray I see the "N/A" and I have to update it manually.
This will happen if your computer does not have an Internet connection before Weather Watcher Live attempts to retrieve the weather. Try enabling the "Pause 30 seconds before retrieving forecasts..." checkbox in the "General" section of the Weather Watcher Live Options window. That should give your computer enough time to establish an Internet connection.