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I'd do "Jr." The Rockefellers are up to John Davison Rockefeller IV (he's Senator Jay Rockefeller of West Virginia) and they seem to keep things straight by their numbering system.

In our family we distinguish by changing the middle name. As it happens signatures are almost identical (the acorn does not fall far from the tree, I guess). But I am aware of only one case in 60 years when the signature of JBoa was confused with that of JCBoa, and none in 45 years when that of JCBoa was confused with that of JABoa.
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