Do item payoffs add up? (Trading madness!)

I notice a lot of the Bell Door guards want either this OR that, and I'm afraid if I chose the alternate option, I'm not going to have the items for ANOTHER door person!

Do all the items you find fix this? If I spend my items on one guy, can I find more to pay off the other?

Is there any moments I should worry about that might screw myself over from 100%? These sprites are quite.. finicky.

You have enough of everything, but there might be a special treat if you manage to sneak past all of them without paying

oh no.. I'm screwed..
ah well, at least I got the gauntlet done.

It's very hard to sneak past them without paying though, and not really intended for your first playthrough I think you'll get most out of the game if you play it without worrying about that the first time, and the second look into 100% completion (which by the way requires that you make the official sandwich - vegan/allergy substitutes are allowed).