A couple players in my league had noticed this so one day I decided to test it. Find a race to spectate or do it on one of your own. Before the race starts, load both the Live Timing and 2D viewer for the same event, and open the chat window on 2D. Type a message and send it: it doesn't show up. Switch to the Live Timing, and your message is there, as are any messages sent by other players. But if you switch back to 2D, there are no chat messages, only joins and departs. Once the race starts, the messages (sent and received) work as they should.
2. Wind Direction is always displayed as North.
The 2D viewer seems to retrieve the weather data properly:
WeatherMessage[description:Cloudy tempertatureC:26.0 windDirection:0.875 windSpeedKph:25.749504 iconUrl:http://igpmanager.com/play/content/misc/igp/image/weather/cloudy.gif]
WeatherMessage[description:Cloudy tempertatureC:16.0 windDirection:0.625 windSpeedKph:0.0 iconUrl:http://igpmanager.com/play/content/misc/igp/image/weather/cloudy.gif]
(pulled from Java Console while spectating two different races)
... but when you click the weather icon at top left, the direction is always displayed as North.