I really underestimated this card. Winging It is one of the best clue gathering tools around for Survivors. -1 Shroud may not seem like a lot, but it makes any 3 Shroud location "Look what I found!"-able: when played from the discard pile, you can guarantee you'll net 2 clues from a 3 or less shroud location. Even better- this shuffles back into your deck after being played from the discard pile, so you can simply Drawing Thin yourself into it over and over again.
This is especially nice for people who don't have hand slots to spare for Flashlight or Lantern. Rita Young for example likes using both hands for Baseball Bat and Ornate Bow. Similarly, William Yorick builds sometimes rely on the bat and Old Hunting Rifle. Survivor versions of Tony Morgan should probably consider this card as well since Tony will likely have his hands full with a pair of Colts.
Both Wendy Adams and "Ashcan" Pete can use their special abilities to throw it in the discard and get the better activation of the card earlier. Calvin Wright can use it to help delay Voice of the Messenger slightly (along with Impromptu Barrier and Improvised Weapon). If trying to keep Calvin as trauma light as possible for future campaigns, this seems like a pretty necessary way to go about it.