How far do you fill it up? I don't know- I have run mine dry so far. However, on general priciple, I would think it needs only have the largest gear dip into the oil- the oil will climb to the rest of the gears....provided conventional oil is used...and I would not see a reason to use anything else. Synthetic gear oil does not climb as well which is not a concern in a pressurized oil system, but is a concern when lubrication requires the oil to cling and climb. I personally do not see a need to bathe the clutch, but I would like oil on the gears. Others want the clutch to run in the oil....so far, I do not think there is any consensus.
As for making the drain hole leak proof- the same way a drain plug on a car does not leak- drill the hole, thread it, and plug it with a bolt, washer and rubber washer.