Re: leak in lower unit
Milky oil is a sign of water. When you first take out the bottom plug screw you should look closely to see if what looks like almost straight water comes out first, since any water should theoretically move to the bottom of the mixture. In any event, you could simply have a bad washer around the plug screws. I would probably change those, refill it with new oil, and keep a close eye on it next year (check after each use kind of thing) to see how bad the leak is, if it still leaks at all.
As for the lower unit not draining. That would most likely be exhaust crud building up in that part of the motor over time. Whenever the motor is left tilted up, the unburned oil that builds up in the exhaust will drip down into this area and turn into a form of sludge. You could try poking it with something to see if you can get the water to start to drain out, but the best way is to remove the lower unit and clean it out from above. You need this unclogged because this is where the water from the water pump drains out. If you do not get this to drain and the motor goes below freezing, some serious damage may result.
