Maybe it would help to spell out II as "The Second" or IV as "The Fourth"? People with hyphenated or apostrophed last names could even spell out their punctuation too. But then how do you standardize on the spelling of punctuation?

FORTH solved the punctuation spelling problem by systematically documenting how every word (including punctuation) is pronounced, so you could unambiguously speak FORTH programs over the telephone.

http://forth.sourceforge.net/standard/fst83/fst83-12.htm

-Don O Apostrophe Dell Hyphen Hopkins The Fourth (Not to be confused with Don O Tick Dell Minus Hopkins The FORTH)