Search this post for "pumpkin locations" should pull up the post that tells you where each is. I used it earlier when I replayed from the beginning after downloading 99.1.Where and how do I find the key to the video room and where are the last 2 pumpkins
The key for the video room you get from a bum between your normal house and the basketball court. Usually in the afternoon/evening. It randomly trips once you have moved some of the other stories along. It used to be the trashcan in front of your main house but think that got changed somewhere along the different version. He will just give it to you. You will need a high enough courage ranking or you won't talk to him.
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