I have a 'Tip' Charles in my family who I strongly believe is the same one you are looking for. Tip was a younger brother of my great-grandmother, Pricey Charles-Slone. They were the children of John Charles & Susie Charles-Charles. John & Susie had at least 13 children, another being 'Joseph' Cleveland Charles that you mention in your posting.
On Tip's WWI draft card his name is listed as Ireland Tip Charles. On Census records he is listed as 'Cleveland' Tip Charles.
I also show that Tip married Sara Chapman about 1916. They had two children: Gracie and Eugene Anthony Charles.
Sara married Tilden Goff after Tip's death and had four more children.
I would love a copy of the photo you have of Tip and I am happy to share information on the Charles family.
I wondered what happened to Tip, I assumed he died of either an accident or illness, thanks for your information.
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