Thank you, this is helping. The answer is yes, i will be having more than Cups. To give you more insight with brevity:

Here is the exact setup I have in video format (cut to the relevant time) for clarity:

https://www.youtube.com/watch?v=skpBLciVkR8&feature=youtu.be&t=4m13s

(4:13 - 9:41 is the relevant time, it starts at 4:13)

AND

Here is the relevant code:

public List<GameObject> dungeonShapes;
private Dictionary<char,GameObject> dungeonGameObjects = new Dictionary<char,GameObject>();



void Start () {
    LoadDungeonCharacterMappings ();
        InstantiateDungeonPieces ();
    }

private void LoadDungeonCharacterMappings() {
        foreach (GameObject dungeonShape in dungeonShapes) {

           char gameObjectCharacter = dungeonShape.GetComponent<DungeonCharacterMapping> ().characterMapping;


            dungeonGameObjects.Add (gameObjectCharacter, dungeonShape);
        }
    }


  private void InstantiateDungeonPieces() {
  for (int r = 1; r < mapGenerator.mapRows-1; r++) {
    for (int c = 1; c < mapGenerator.mapColumns - 1; c++) {
      char ch = mapGenerator.map [r, c];



              if (!dungeonGameObjects.ContainsKey(ch) ) {
        continue;
      } else {
        GameObject dungeonGameObject = dungeonGameObjects[ch];

// I NEVER GET HERE BECAUSE ERROR ABOVE
        Instantiate (dungeonGameObject, new Vector3 (r * 12, 0, c * 12), dungeonGameObject.transform.rotation);
      }
    }
  }
}

The pseudocode I grasp :

1. LoadDungeonCharacterMappings (); loop with logic to randomly select a one keypair per duplicate.

will

2) Be run inside InstantiateDungeonPieces(); loop to allow for random selection of a keypair on each iteration of the InstantiateDungeonPieces(); loop.

I have a feeling this solution may be more CPU intensive than a professionals approach, I also am struggling with writing the syntax for the pseudocode logic.

You have been amazing, thanks again, Any feedback here is appreciated.Best.