Every investigator who can take Lockpicks (0) can take Lockpicks (1), right? So, sure, these kind of stink, but you'll get to upgrade to the Level 1 one soon enough. Well, not so fast, it's level 0, so there's Versatile and those crazy Dunwich investigators, so let's talk at length about those. Ah, who am I kidding, this review is about Monterey Jack, our lovable Rogue who can take only level 0 Rogue cards, so it's this card or no Lockpicks for you unless you're friends with a traveling salesman.
The effect is strong, as with the level 1 version. You're adding your two highest skills together, for a base 9, always. It'll only get you one clue per turn, which is okay, but you're really adding this to your deck to trigger the succeed-by-two effects, since indeed you must succeed by two. So, trigger your Lucky Cigarette Case to draw some cards, make some money with Gregory Gry, or throw a Quick Thinking at the test to get another action. Or once you get some XP, Deduction (2) solves the "only one clue" problem too, and Perception (2) will run you through your deck to get all of those cool skills back again.
OK, the downside. First, the auto-fail. You don't get your clue, you don't get whatever bonuses you were hoping for, you get nothing and your Lockpicks end up in your discard pile. This is bad, but is that really much different from playing an expensive event that auto-fails on you? You probably got SOME use out of this card, unless you pull the auto-fail on your very first activation, and you're out two actions and 3 resources for nothing. That's Arkham! But remember, the red token only shows up 6% or less of the time!
Now the non-autofail cases where you'll discard the asset: you can fail the test and get nothing or pass the test and get a clue, but in either case you didn't do math properly or are taking a big risk. When deciding whether or not to take Lockpicks (0) , you need to heavily consider the chaos bag and your campaign. The highest regular shroud is 4, and these usually only have 1 clues. 2 and 3 shrouds are far more common. At base 9, being up by 5 means that you're fine if you draw the -3 even on the 4 shroud locations. That's the usual situation for Easy. For Standard, you're likely to have a -4 or -5 in the bag. It's simple enough to commit one of the above skills (don't forget, or icons only) or two to cover the worst tokens. Opportunist lets you cover the spread every single turn. Keep an eye on those tokens, too, which can get nasty in some scenarios. The unpredictability of tokens probably makes them a bad choice if you're worried about losing the Lockpicks. Frost tokens are a problem, too -- the -1 for the first one is probably not a big deal, but the second is an auto-fail, so.
You have two more options to get your stats high enough to succeed which are easily accessible to Monterey Jack. First, add a static boost! Either or work, so we're talking about Hiking Boots or Death • XIII or Gené Beauregard. Or pay some money: Streetwise (0), Higher Education (3), or Hyperawareness (4) are fine choices -- or even Crafty, which pays for the price of Lockpicks, too.
For Monterey Jack, this should not be the only way to get clues in your deck, but it can be an ideal way to make the rest of the deck work well. At base 9, losing the asset is rare, even rarer when you can easily boost your stats. And when it does happen, with Seeker draw you are well on your way to finding your second copy, or reshuffling your deck and getting it back.