I'm glad you pointed out that the size of the person is part of the 2X12 thing. I'm 190 pounds and 6'1". The 2X12's allow me to wiggle underneath enough to check things out. I have at times drained the oil without raising the car at all, although I would rather get underneath to look everything over.
By just reaching underneath without the car elevated, you can remove the belly pan and the drain plug. I would suggest you do this in your old clothes, not that new Hart, Schaftner and Marx.
My comment about oil temperature is based on watching the oil temperature guage in my Vette. The Vette has an oil cooler and might be thermostatically operated. In that car the oil temperature after about 17 miles or so will stay above the coolant temperature by about 20 degrees. You must have an oil temp guage on your Benz.
I read somewhere a few years ago that it typically takes 17 miles of driving for the oil to reach operating temperature. I have found this to be true in watching the oil temp guage on the Vette. Draining or drawing the oil at operating temperature helps greatly in getting the maximum amount of contaminants to come out with the oil.
I believe you could do a better job removing HOT oil out the top than draining COLD oil out the bottom or otherwise remove it.