The front seal on my L3000DT leaks a bit of oil now and then, sometimes I see a small spot on the floor of the barn. One time I over filled the front axle but drained it back to what was a little over full, that was about 8 months ago. I haven't seen any leaking since then.
I am sure over filling can put more pressure on the seals but I don't think they would fail to the point of all the oil leaking out in two hours time. For the wheel to stop turning that quickly I assume the damage to the bearings had to have been done prior to the seal being changed.
The manual on my tractor says that I can use 90w gear oil which is a little thicker and would not be as prone to leak as the UDT will.
Randy