Hey stonerhash
1. Upwind would probably suit you better for the time being, then when you get the hang of it you can play around with them.
2. Yes
3. The two gray lines are there to replace your front line bridles for 1-1 connection for a more C kite feel you must weigh 150lbs or less
4. The fast, medium, slow settings are on your rear lines. If you feel like the kite is moving across the window to quickly for you, adjust your rear lines accordingly.
Lastly don't go getting stoned on hash before you kite

!!!!
Cheers Murph.