Sounds like there is an oil leak someplace. With the amount of air that blows oil around, it is difficult to tell where a leak is originating, unless you clean all of it off, and verify the levels in the gearboxes, and drive it around a little bit, not too long, and see where it is comming from.
could be:
Any of the gaskets or seals on the trans or t-case, could be engine oil that has blown rearward, and collected on the drain plug that you have noticed, could be a small crack in one of the gearbox cases, and it is slowly leaking out..
I had a guy bring a truck to me that had a small leak from the t-case, he said that he needed to as oil every three to four days...He could not figure out where it was comming from...turned out that the nose cone had cracked, and all but complelty fell off the t-case..Gotta love those older Cruiser cases!
Drive it. If it is not making any wild noises, do not let the leak drive you away, unless it is obvious that this vehicle has had a hard life, in which case, if you are looking for something nice, I would shy away from it.
Being on a computer in MN does not lend too well to telling you what is going on..Pics help, but sometimes do not relate the whole story either.
Good luck!
-Steve