I think we can all agree addition is fairly easy. Multiplication, since it can be explained in terms of addition, it also not really that hard. Subtraction and division are harder, as I originally noted, and by extension division, are harder, as there is not one simple rule for conversion before subtraction that won't require additional conversions unless you go to the simplest form, which is unwieldy (along string of I's).
From my example, which was meant for subtraction, not addition or multiplications, we get the following:
XLII - XIII
so we convert to an optimized form for arithmetic (which is, as I've noted a second format you need to know and keep track of, since it's not valid Roman numeral format
XXXXII - XIII
then we note that we have to borrow from the X "place", so let's do that
XXXVIIIIIII - XIII
now we can actually subtract
(XXXX - X) + V + (IIIIIII - III) = XXX + V + IIII = XXXVIIII
Now we have to convert back to valid Roman numerals
XXXVIV = XXXIX
This is using common current arithmetic techniques. I'm not sure whether this is the method they would have employed, or whether it would have been a different method that could have been easier or harder depending on how it combines with the attributes of this number system. Important things to note about the method shown are a pre and post conversion step (or steps, if you don't get every sub-conversion right initially or don't go to a lowest common format), and then the arithmetic itself requires more borrows.