The 2 stroke motor oil is strictly for mixing with the gas, though a high quality 2 stroke oil is highly recomended over the generic brands. A search will yield more advice than you'll ever want to know on the subject. For the trans, regular 10-40 is often spec'd by the manufacturer. Many folks run ATF (Type F) or 80w gear oil (not to be confused with 80/90w hypoid gear oil(rear end)). Again a search will give you loads of information on trans oil.
If the threads aren't totally wasted on the oil drain plug, I'd try using teflon tape to try to seal it. Oil and gas breaks silicone down and is pretty much useless in this application. A better solution would be to re-tap it a larger size or use a thread insert.
If the threads aren't totally wasted on the oil drain plug, I'd try using teflon tape to try to seal it. Oil and gas breaks silicone down and is pretty much useless in this application. A better solution would be to re-tap it a larger size or use a thread insert.