1 - possibly not. As soon as you start the engine the old and new fluid would be mixed so you would never get all the old fluid out, there would just be less and less with each drain.
You would have to disconnect the pipe going back from the cooler to the transmission, start the car and let out 1 litre. Stop the engine, add 1 litre then repeat until you see clean fluid. This may be difficult in your case because your fluid will probably be very clean anyway.
2. Drive the car for at least 15 minutes. Park on level ground. Slowly move the selector through all position down to L and then back to P pausing 1 second at each position. With the engine still running check the level against the HOT range on the dipstick.
4. Good enough.
5. Not sure, I will try and find out the best way. Use T-IV fluid.