Answer:
Today we would convert 499 into Roman numerals as CDXCIX which makes it almost impossible to perform any kind of arithmetical operations with them.
But the Romans themselves would have calculated the equivalent of 499 on an abacus counting device as CCCCLXXXXVIIII and probably simplified them to ID (-1+500=499) in written form in the same way that IIII and VIIII (4 and 9) are simplified to IV and IX respectively.
So the equivalent of 1776 -499 = 1277 would work out as:-
MDCCLXXVI -ID = MCCLXXVII
The above calculation is achieved by adding I to and subtracting D from MCCLXXVI. Remember that a minus minus becomes a plus so -(-I+D) = +I-D