The nail guns are handy and nice, but can have problems of there own, not often, but have had nails curve and come back out, or crumple, and double nails.
but if hand nailing is desired one can make a nailing shield by using a piece of hard board and drilling a hole larger than the nail to be used, or a piece of peg board, and after starting the nail slip the shield over the nail and nail it in to the point where it nearly flush with the shield and then used a nail set to set the nail in to the trim. I have use a old shim as well, not as durable but works. and nearly any thin scrap of product will work to make a shield out of.
a link of one
http://www.thisoldhouse.com/toh/skill-b ... 29,00.html