An extractor will remove the oil in the oil tank. I can't speak for the V-twins but on the 1330 ACE engine one of the reasons you have to check the oil level within a minute of shutting off the engine is because after a minute some oil begins to drain back into the crankcase from the oil tank. You can't get the siphon tube from the extractor into the crank case so you have no idea how much oil you are leaving in the engine. IMO, a pee poor way to change oil.

FWIW, when changing the oil on my Spyder I always stuff some paper towel up into the void where the crankcase plug is and push it rearward a bit to prevent oil from getting onto the plastic pan and I've never had a problem.