Consider all two character valid roman numerals like IV, VI, IX ... up to MD.
Insert some letters in between the characters to tranform it into a valid word of shortest length and longest length for each numeral . An example is the word INDEX corresponding to the numeral IX – while this may or may not be the longest or shortest word.
**** Only valid English words are allowed. No proper names, abbreviations, acronyms, slangs or archaic words.