Mine just kind'a came to being. I didn't spend a whole lot of time at it... maybe I should have.
I did spend some time trying to decide if it was a "Railroad" or a "Railway". Initiallly it was a "Railroad" but in working on the logo I could not get the "Y" to nest neatly inside the second "R" or "RR", so I tried "RY" and I thought it looked good that way.
I have had some fun with folk that ask what "CMBY RY" stands for. It is fun to watch them count on their fingers, first they count off the letters one at a time while they mouth the letters.... "C", "M", "B", "Y"... then they count on their fingers again saying, "Chicago", "Milwaukee", "Burlingon",... uh.... uh.... "What does the 'y' stand for?" When I suggest it might be "Ypsilanti" people just say, "No, it can't be that." If I suggest "Yukon" their eyes look off into space as if studying a wall map of North America and then they say that is too far and makes no sense. The suggestion of "Yokohoma" doesn't work either. "There was never a railroad to Japan!", so it seems nobody will accept a fictious name if it seems to be outside of reason. Of course, most people have no idea how many real railroads had names that bordered on the ridiculous.
I eventually tell them what it really means ("Charlie McCullough's Back Yard Railway") and it is then that I learn I should have spent more time picking the name.
I do find it interesting that so many people have never seen "RY" as the abbreviation for "Railway". Several have said it should be "RW", but I have never seen that, though I have seen "RWY". My daughter had a very nice sign made and the maker convinced her that RY stood for Rail Yard, so I have a sign that reads "CMBY Rail Yard". That's okay, all Railways need a Rail Yard!