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.