Thanks Michael, that is a great help.

I had not checked the Square in Circle mold owned by Portland Card Company. I just now looked at the chips on that mold on the ChipGuide, and founds some more, a couple of which I have posted below. Since there are records for a lot of those chips it will be interesting for me to look up when they used that font. According to the Gaming Table the Gracie's chip you posted is from 1991-1994, of the chips posted below, the Elbow Room from around 1977, and the Marina Cay Resort from the 1990s.

Those Portland chips will give me a lot to look through, and it will be interesting to see when they started using that font. They did sell some chips in California, and it makes me wonder if they were associated with the SqSqRt mold chips with that font, or if that will remain a mystery.