In the original source code and Sluicebox decompile alike, things are a little clearer.
Look
You have a certain number of quarters, tracked by global 168 gQuarters. In American English parlance, a quarter is also known as two bits, as in the price of a shave and a haircut. Therefore, if you have one quarter in change, looking at the item says "2-bit game player". The number goes up accordingly, so if you have four quarters you're an 8-bit player. Unfortunately, you can't have four quarters as the number is only directly assigned 2, 1, or 0, not incremented.
Do
Nothing to say about this. A quarter has only two sides and it picks one at random. It has nothing to do with the Look description.