Sr, Jr, III, IV
Question: If for instance, my grandfather was John Moe Doe Sr; my father was John Moe Doe Jr; and my brother was John Moe Doe III. Then my brother named his son John Curly Doe which broke the Sr, Jr, etc line. Would it be proper for John Curly Doe to name his son John Moe Doe IV?
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Replies

Perfectly fine. An Continuing on from your example, if John Moe Doe IV named his son John Curly Doe after his father, he would be right to be called John Curly Doe II, however John Curly Doe the elder wouldn't be referred to as J.C.Doe Sr.
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It's not as common, but it would be fine for John Curly to still name his son John Moe IV. I've known people named that way-- a boy named for his grandfather.
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