Shire Lookout Point serves a very specific purpose: to give the Free Peoples player a guaranteed Gandalf's Cart from the beginning of the game. This is useful for a fellowship starting Frodo and Gandalf but nobody else; all the equipment of other companions can be stored until needed using the cart. It can be helpful for larger decks, as it might be easier to bid for the site than to use four copies and wait to draw the card. It depends on going first however, so a high bid may be required. It can be useful for a Grey Wizard fellowship playing a lot of Gandalf signets, or a Friend of the Shirefolk fellowship with many races.