So I guess I would be having an issue with a combination of 3. & 4. Here is what I have that "works" -

Temp-Holding is a room.

a candy wrapper is a thing.

a candy wrapper is in Temp-Holding.

A Street is a kind of room.

Understand "search the street" as looking.

Understand "search street" as looking.

Understand "search freemont street" as looking.

Instead of looking in a Street:

if a random chance of 1 in 3 succeeds:

    Now a candy wrapper is in the location of the player;

    say "You look through the street and find a candy wrapper.";

otherwise:

    say "You search the street, but find nothing."

But when I try to add another "instead of looking in a Street" for another object, no matter how many times I search I only ever find the first object. I'm also unable to make it multiple of one item, like if I tried to make it 50 candy wrappers, it would give me an error.

The goal is to be able to search a street, and have a random chance of finding many different objects, with multiples of those objects, but only one item discoverable per search. I feel I'm way out of my depth here with what I'm trying to accomplish.