I've been trying this week to puzzle out a little of this old building's background --- without actually going to the trouble of doing the research that would tell more. It isn't working very well, but a few things are obvious. And I'll get around to searching for the rest of the story --- eventually. So the word "analysis" is used very loosely here.
It's call the Hotel Charitone Annex because the developers of the hotel purchased it during the early 1920s and as the four-story hotel was being built next door punched a door through into its upper level and redeveloped the space there as additional hotel rooms.
Before W.D. Junkin and H.D. McCollough purchased the vacant lot where the Charitone now stands, this buidling housed a smaller hotel, the White Front, operated by Elizabeth (Mrs. J.O.) Crips, although she may not have owned the building. Mrs. Crips also operated the White Front Cafe in the building and seems to have resumed its operation in 1925.
"White Front" is a little puzzling because, obviously, the building does not have a white front. However, the current facade is much newer than the rest of the building and probably replaced something substantially different. Because the facade's brick, brickwork and detailing do not match that of the Charitone, it probably predates the hotel building --- although not by much. It looks like something that might have been added after 1910, perhaps, but before 1920.
If you walk around the building, you can see that the main structure is much older, dating most likely from the 1880s. The window headers are arched, for one thing, and the quality of the brick substantially different and laid in a different manner than that of the facade.
I'm intrigued by this arrangement of what probably was two windows and a door in the northwest corner of the building, bricked up and punched through to form what looks like it once was a loading dock.
The building now is owned by Hotel Charitone LLC, which is redeveloping the hotel, but is not a part of the Charitone project in part because it was acquired after planning for the Charitone commenced. I'm guessing the Annex will be touched up, then held in reserve for further redevelopment.
It's also going to be interesting to find out more about the Crips. They had arrived in Chariton from Ottumwa prior to 1900 with their adopted daughter, Mattie. He was operating a "lunch room" here during 1900 and she, a boarding house on Auburn Avenue in both 1900 and 1910. John Crip's metal health seems to have started to decline during the first decade of the 20th century. His business was sold during 1906 and he was institutionalized during 1908, a year after their daughter died.
Although John returned home, Elizabeth is listed as head of the family thereafter and probably was forced by circumstance to go into business herself. She became proprietor of the White Front at some point between 1910 and 1920 while remaining active in civic affairs, including the Chariton Public Library. John died during 1924 and is buried in the Chariton Cemetery. Elizabeth died 10 years later and presumably was buried by his side, although by that time there was no one left to mark her grave.