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The largest number you can write using Roman numerals without an overline at any symbol is 3999 (MMMCMXCIX), and the largest possible number is 3999999 (MMMCMXCIXCMXCIX, with an overline over the first nine letters.
The largest number roman numeral that begins with the symbol "V" is "VIII" which represents the number 8.
There are some places where four is IIII rather than IV. But that's not exactly proper. You shouldn't ever run into an occasion where you need 4 or more symbols in a row without being able to use a different symbol.
4-IV
The symbol "D" can never be repeated in Roman numerals. According to the traditional rules of Roman numerals, "D" represents the number 500. It cannot be repeated to represent larger numbers, such as 1000 or 5000.