|"Mafia look at little child. Mafia see loser."|
This achievement is not overtly difficult in any way, restricted only by the requirement of the Ice Hat and the Hookshot Badge. Since both of these are mandatory for game completion and encountered midway through the game, the achievement can be achieved with relative ease for a majority of players.
Though not much strategy is needed in order to complete the achievement once the Mail Room is unlocked, steps to unlocking both the Hookshot and Ice Hat more efficiently can lead to the achievement to becoming much more readily available. Otherwise it is a very simple achievement that requires minimal input by the player once all the assets are in play.