How does this card work with Scavenging? If I play it from my hand by discarding instead of exhausting, does the discard happen before I make the skill test and perform the action? And because it's in my discard pile, would I then be able to get it back with scavenging if I succeed by two or more?

It seems obvious but as no one has written a review yet ... Use the action on this card to discard Winging It: you gain 2 clues with Nautical Charts and then you can play Winging It from you discard to try to get 2 clues in a single action. If you play a solo deck, you can of course do this with the other Improvised events (Improvised Weapon and Impromptu Barrier).

And use Tool Belt to stack Nautical Charts, Hand Hook and Anchor Chain. Then you need a good card draw to get the events back.