Bob's extremely cool special talent gives us interesting new deck-building options where we can get Survivor and Rogue items to investigators that have never had access to them before. The problem is finding that special talent in Bob's deck.

Searches Bob can do himself to tutor Shrewd Dealings:

• Friends in Low Places 0 resources to play, and 1 resource per card you add to your hand from the results. One of the new customizable cards, but even at level zero, it allows you to search 6 cards deep for any cards with a trait you preselected (here you would presumably want Talent). By far your best native option; thanks to @death by Chocolate for the catch! (Honestly, this is probably one of the best deck searches in the game at all.)

• As pointed out before, Lucky Cigarette Case: 3 XP, 2 resources. After a successful skill test, allows you to search the number of card you succeeded by. This likely won't search many cards at a time. (Edit: moved Rabbit's Foot (3) below. I forgot Bob can't take native Survivor upgrades!)

Searches with support from a Seeker (or someone who can use Seeker cards) to tutor Shrewd Dealings:

• Old Book of Lore, search top 3 cards.
• No Stone Unturned, search top 6 cards

Searches Bob can do by "borrowing" a card from another player to tutor Shrewd Dealings:

• A Chance Encounter, used to steal Mr. "Rook" from a discard pile for a turn, and search the top 3-9 cards, up to three times on that turn. Somewhat convoluted and slow to set up, but it could happen.
• "You owe me one!" can be used to steal a search card from another player's hand and play it for Bob. -- Take Old Book of Lore or Mr. Rook from a seeker and then use Bob's own actions to search his deck, freeing up the Seeker for finding actual clues instead of just helping Bob get his act together. (Can't you just hear the librarians who kindly offered to help Bob search his inventory, aghast at the state of his warehouse? "Don't you ever ORGANIZE anything in here, Bob? How on earth do you FIND anything?")
• Take Rabbit's Foot from another survivor (the upgraded 3 XP version). After a failed skill test, allows you to search the number of cards you failed by. This option is cheaper and maybe easier to trigger than Lucky Cigs, but with Bob's baseline at 4, he doesn't have a great option to fail badly on tests that don't have any negative repercussions. So you probably won't be searching super deep this way.

Mandy's ability to enhance any search by an additional 3 cards would obviously be quite helpful to Bob, with the latest 50-card deck taboo, I'm not sure anyone will actually play Mandy anymore.

Edit to clarify: There are indeed many other search cards that can help Bob find and recur items and other assets, but this list is specifically regarding ways to tutor Shrewd Dealings, not other assets.

It's a fairly expensive (in xp) skill card, so it's pretty easy to just avoid it. The fancy thing it does is 5 xp for Always Prepared, which is a lot even if you've got 2 copies, and it's limited to once per round. Usually it's pretty similar (+/- 1 symbol) to Unexpected Courage, and the traits portion limits it to monsters or treacheries, and can't be used to investigate or do tests on location cards.

Humanoid and Monster traits will get you a card that's useful against a bit under 100% of enemies, and enemies are only around 1/3 of the encounter deck. Adding Elite and Ancient One means it will give you 5 symbols against most of the more difficult monsters. The good news is, those 4 traits will get you almost all enemies (and double coverage against difficult monsters) in all campaigns for 3 xp. I'm not sure what combo's you would need to cover all of the tests in the encounter deck, but I can't imagine 4 traits would be limiting if you're careful.

Nemesis instead of Always Prepared (or with fewer traits; elite covers the monsters you'd want to use it on) sounds useful if you're willing to have a card in your deck just for fighting difficult monsters. Not a bad plan.

If you can find the traits that cover all of the really nasty treacheries, Mythos-hardened might be a way to thin the encounter deck. But that requires knowing about them ahead of time.

Some example cases of using Yorick's to replay an asset that could defeat the enemy as well as itself going to the discard pile :

• Knife : Discard Knife: Fight. You get +2 for this attack. This attack deals +1 damage.
• Beat Cop : Discard Beat Cop: Deal 1 damage to an enemy at your location.
• Lantern : Discard Lantern: Deal 1 damage to an enemy at your location. This action does not provoke attacks of opportunity.

Can play the same Knife/Cop/Lantern from discard pile if the attack defeated an enemy, since discard before colon sign is the cost, while the effect is occurring it is already in the discard pile.

• Beat Cop (2) Exhaust Beat Cop and deal 1 damage to it: Deal 1 damage to an enemy at your location.
• Aquinnah : When an enemy attacks you, exhaust Aquinnah and deal 1 horror to her: Deal that enemy's damage to another enemy at your location, instead. (You still take horror dealt by the attack.)

Can play the same cop/Aquinnah from discard pile if the self damage/horror is lethal to the cop/Aquinnah and 1 damage also defeats an enemy. Self-damage/horror before the colon sign is the cost and is completely resolved including putting the cop/Aquinnah to the discard pile. Only after that you deal 1 damage to the enemy.

• Guard Dog : When an enemy attack deals damage to Guard Dog: Deal 1 damage to the attacking enemy.
• Brother Xavier : When Brother Xavier is defeated: Deal 2 damage to an enemy at your location.

Cannot play the same dog when using reaction on its last health to defeat an enemy. Since enemy's damage is not the cost of this reaction trigger. The dog and the enemy are waiting to go to the discard pile together as an impact of the "when". "When" is always after the condition but before the impact, it is not possible to partially wait for dog + enemy to impact (go to discard) before adding in Yorick . Xavier works similarly.

• Baseball Bat : Fight. You get +2 for this attack. This attack deals +1 damage. If a or symbol is revealed during this attack, discard Baseball Bat after the attack resolves.

Cannot replay the bat as Yorick on ST.7 but the bat is discarded on ST.8. (Timings)

Special mention : Graveyard Ghouls - He can trigger on defeating it. Graveyard Ghouls stops engaging him at the same ST.7 as his , card can now leave his discard pile.

The longer you look at this card, the better it gets.

Say you're running this as a having option for your bruiser oriented survivor. Ru ln6 0 ok l

A single action 6 heal per investigator is huge and unrivaled by any card. Sure, you have to drop a doom. But I would challenge you and figure out any other way to heal 3 damage/3 horror from your investigator in under 3 actions. The doom also does not auto advance, so you can get lucky and suffer no downsides for this at all if you get a witching hour draw.

Then comes the other use for the card... taking mild damage and horror to push the clock back one. As long as you have another healing ability (like Spirit of Humanity) this is an outrageously overpowered option. Compare it to other cards (like Golden Pocket Watch) which require you to draw, play and pay for it, this only requires a draw, for five less experience.

Overall this is a very powerful card with a great amount of flexibility and very few downsides.

In solo it wasn't bad to include a couple of these in a deck for Rita Young and the like, even though she can't really recur it outside of Resourceful etc. But with the advent of Crafty, I can see an argument being made for having this in hand as a starting supplemental 'weapon' by some survivors even in multiplayer. I'm using it with Rita Young in a 3-player right now, and having 1 Crafty - or even better, 2 - to both pay for the play of this card and amp up your Fight to as high as +6 means you can take out monsters with that little bit extra. Even the Clover Club Pit Boss can be a challenge if you're Rita as main monster manager. Elite so can't Waylay, so use a Cheap Shot for 2 damage and you've got 2 left to go. Fighting 3 on 3 doesn't set the world on fire. But use the Gravedigger's Shovel with Crafty and you can rock out two actions of 3+2+1 = 6 v 3, beating the Cultist on Standard.
Not the best weapon, but still a fun one when Rita can deal 1 Damage with a standard evade and a very reliable 1 Damage with the Shovel.