Adding and subtracting Roman numerals is pretty easy because it's all addition and subtraction. A lot of it is just repeating the symbols just like with tally marks. X+X is just XX for example. You do have to keep track of when another symbol is appropriate, but VIIII is technically equivalent to IX. It's all the other operations that get harder. If the Romans had negative numbers, then the digits of a numeral could be viewed as some kind of polynomial with some positive and negative coefficients. But they also didn't have that.
>The notation itself doesn't really make a difference. We could call X=1, M=2, C=3, V=4 and so on.
Technically, the positional representation is part of the notation as well as the symbols used. Symbols had to evolve to be more legible. For example, you don't want to mix up 1 and 7, or some other pairs that were once easily confused.
>Why did the Romans not think of it?
I don't know. I expect that not having a symbol for zero was part of it. Place value systems would be very cumbersome without that. I think that numbers have some religious significance to the Hindus, with their so-called Vedic math, but the West had Pythagoras. I'm sure that the West would have eventually figured it out, as they figured out many impressive things even without modern numerals.
>But good notation is backed by a meaningfully different way of looking at things.
That's just one aspect of good notation. Not every different way of looking at things is equally useful. Notation should facilitate or at least not get in the way of all the things we need to do the most. The actual symbols we use are important visually. A single letter might not be self-describing, but it is exactly the right kind of symbol to express long formulas and equations with a fairly small number of quantities. You can see more "objects" in front of you at once and can mechanically operate on them without silently reading their meaning. On the other hand, a single letter symbol in a large computer program can be confusing and also makes editing the code more complicated.