You have to remove both the lower and upper plugs to get the oil to drain out with any speed. There is only a small passage to allow the oil to go from the bottom to the top and for the oil to run back out. And yes you need to fill it from the bottom up to get the air out of the lower. The one marked vent is just that, it let's air in to drain it and air out when you fill it.
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2011 SUNDANCE B20CCR SKIFF, 2011 YAMAHA 90HP 4 STROKE, 2011 KARAVAN SINGLE AXLE ALUMINUM TRAILER, LOWRANCE ELITE-7 HDI, MINN KOTA RIPTIDE TROLLING MOTOR
2000CC HYDRA-SPORT 225+HP EVINRUDE SOLD 
AND THE PINK JEEP!!!! R.I.P.
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