[The Squatter of Amon Rûdh]

To be fair, Tolkien doesn't say that the first group were killed in the battle: they might have been so deadly that they began a lucrative career as mercenaries and assassins. The second group were fighting in a victorious army, so I'm not sure that says much other than that hobbits are good at choosing sides. It does seem unlikely that hobbits would ever have enough martial spirit to make good soldiers, though. Sadly, it's also quite probable that any money saved on footwear would have to be sunk into rations, so I'm not sure how much of an advantage their barefoot predilections would be either. I suppose one could always feed them their boots.