Here are all the things Bob can toss folks.

This card obviously gets stronger when you understand your team's deck and can slot specific things to give them a hand, you know, toss an Eye of the Djinn to Patrice, get Cho some Crystal Dreams, ect. These kinda effects are sorta a pain to talk about in a venue like this, and not with your buds while your planning your deck, so they don't get a ton of love here.

But Bob HAS to run this. And while the 1 resource discount is nice for him, because he needs to run it, it is important to look for 'generic' uses of it that don't require specific deck knowledge that may come in handy.

One thing that jumps out at me is that Bob has the potential to be a fairly strong 'healer' when it comes to physical damage, between Bandages and Leather Coat which both let you toss a 3 (or together, 6 or even 9), HP buffer onto a character in crisis. Bullet Proof Vest becomes really attractive on him as well: a 1 resource, heal 4? Nice!

He can do alright at healing horror too, with Keepsake and maybe Grimm's on a character liable to faceplant tests, but Grimm's is questionable and Mr. Pawterson takes up a more contested slot than Coat does. Elder Sign Amulet likewise could be a nice thing for him to toss into his deck to help buffer for lower sanity folk. And hey, if you are about to die to horror, the fact its an important slot low key doesn't matter anyway: if you are sitting at 1 horror it doesn't really matter how much you like your Cig Case or Fancy Mirror or whatever: you will be glad Bob is offering you a 2 or even 4 horror 'heal' right then and there.

Ultimately though, Bob is a dedicated multiplayer support character, more than anyone else in the cast (though we all just know someone is going to find a way to clear Devourer Below on Super Ultra Double Expert Arcade Edition with him solo!) because both his personal ability and his signature reference other players. So it truly does pay to be cognizant of them, even though you probably shouldn't build decks where someone NEEDS something from you.

Got a lot of rich characters who tend to not use their hand slots and could use a good trash clearing tool because they aren't swole enough to punch rats away bare handed? Toss your friendly Ursula or Sefina your spare Fire Axe. Got a Fin playing flex? Toss him your spare kicks too while your at it. Give Mandy (or most seekers really) a Lucky Cig Case to help them get their crazy combos out faster and end the scenario sooner.

Bob can't ever guarantee anyone he is going to be able to toss items to them unless he goes out of his way to get more effects that allow people to swap things around, so you shouldn't build around this specific card if you want to setup something nuts. Instead, you need to use your game knowledge and understanding of what other people might want, but not need. If you do get that Dream Crystalizer for The Boxer, make sure you have enough events yourself with useful symbols on them so that you can use it as well in case you just brick on finding this thing, and make sure Nathaniel doesn't skimp on skills just because you MIGHT be able to give this to him. You tossing an item to someone should make the scenario far easier, rather than you failing to toss someone something making someone's deck fall apart.

In essence, you need to be a good salesman: the stuff your hocking needs to be things people never even knew they needed, but the second you offer it to them they realize they realize life is going to be so much better with it.

The Good, the Meh, and the Ugly:

The Good: A dollar off all items? Fantastic. It's doesn't even exhaust. Between this and Bob's free play-item action, you've got a mini Ever Vigilant forever.

The Meh: The second bit seems neat; in practice it hits the same barriers as Teamwork as you mess with other deck's plans for their limited Slots. Slotless items sidestep this, so here's hoping this cycle includes more things like Pills, Smokes, Booze... More Booze... uh...

...wow. Bob may be more of a bootlegger than an actual bootlegger.

The Ugly: SO SWINGY. Bob REALLY wants this in his opening hand. Get it anywhere from mid-game on, and you're probably just committing it for an investigate. And to my knowledge, there's literally no tutor that'll help. It feels wasteful to ignore, but risky to count on, sort of like Wendy's Amulet which you can at least find in a Backpack.

(EDIT: Building a Bob deck and realized that L3 Lucky Cigarette Case is an excellent tutoring option available to him, both for this and more or less anything else.)

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So, tl;dr... make friends with your local seeker!

In case anyone was wondering about whether the words "only... under their control" in Bob Jenkins' ability stops you from utilising Shrewd Dealings' activated ability during Bob's additional action, it doesn't... the rules team answered my email query with: "Shrewd Dealings is intended to synergize with Bob Jenkins’ investigator ability—meaning, when Bob uses his additional action to play an Item asset from an investigator’s hand, he can play that Item under the control of any investigator at that location."

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.