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Thats just a normal thing for the original head gaskets. In the 2nd pic, you can see the designed tab thats meant to "weep". Id just re torque the nuts and not worry about it.
Well, nobody knows what your working on yet. I'd guess a 5ton but I'm not sure. Gear oil should not leak out, there is a seal to prevent that, I think.
Some sockets are longer than others. As stated, if the socket doesn't engage the thimble enough, it will cause trouble.
I had one that needed ground down to work on the square.