1) Not sure precisely how long it is but I think you're looking around 6 feet perhaps a bit longer. I have mine hooked up to my DLP via the VGA cable and its a pretty decent length from the console to the port on the TV and there's still a bit of slack. Actually after looking at it one more time there's a lot of slack on there. I'd say there's a good chance of 8 feet, presuming you purchased an MS cable.
2) The system automatically checks for the main dashboard updates upon each boot. Individual game updates are checked upon each game load. Codec updates are done (if needed and not included with the dashboard update) when you attempt to play the codec. Very straightforward. Good chance that you'll have to download one media update to play avi files and the like but not much else.