
I think this card is underrated. Sometimes you would like to soften up a big enemy that has Retaliate for your monster hunters, or that person is you and you can pull out Backstab for your next action, or activate Delilah O'Rourke's ability to finish off a 3 HP enemy (Delilah also gives a +2 skill boost).
But other times you need a test you are sure you can succeed big at for your Rogue succeed-by-X cards, like Momentum, Watch This, Quick Thinking, Nimble, Opportunist, or All In, and you're engaged with an enemy. Winifred & Rita will be testing at a base 8, Tony, Skids, Finn & Monterey Jack at 7, Bob, Trish, Jenny & Sefina at 6. With the aforementioned skill cards that also have a payoff, it shouldn't be hard to succeed by 2 (or by 1 with the upgraded version, which can also return to your hand). Sure you can draw the red token, but that's the Rogue lifestyle.
The other option, Lockpicks (1), is a better payoff for the succeed-by-X cards for Bob, Finn, Wendy, & Trish or Monterey Jack with Lockpicks (0). But don't glaze over Cheap Shot.