Several points to make (from a Cincinnati native):
1) Skyline Chili is the largest chili chain in Cincinnati It is far from the best. They are the worst in terms of giving you any chili on your 3, 4, or 5 Ways and they are generally a poor value.
Gold Star and Empress, the two other chains do a lot better job.
Camp Washington is an independent that serves decent chili. However, many locals prefer Dixie Chili which I believe is in Covington.
Personally, I can make a better chili than most of them at home at a small fraction of the cost and serve it MY way. I think that the ONLY time that my family EVER goes to a parlor anymore is after funerals. The prices at the parlors are ridiculous, especially as the portion sizes have shrunk over the year.
2) The further you get from Cincinnati, the WORSE that Skyline franchises are. The ones in Dayton are edible. The ones in St. Louis, Cleveland and Columbus are horrible.
3) If the chili is made properly, the cinnamon and the bitter chocolate flavors blend in pretty well and are not noticeable.
4) Have to confess that I use a private label mix that produces a chili that is almost as good as the homemade. Ten minutes of preparation, 2 hours of cooking time and everything is done, no problem.
5) In all my years, I do not recall seeing many people pouring habenero or pepper sauce in their chili. I am not saying that it isn't done but I never saw a tobasco sauce bottle in a chili parlor.
6) There is a place near Marquette's campus in Milwaukee that has the chili parloe feel and a chili that is pretty close to Cincinnati chili. It is pretty decent but the prices are outrageous. The guy has to be running at about a 20% food cost.