OK, so after my cycle in this morning, I've a better take on it.
Basically, the problem here is the system, or a representation problem. In this instance, we are unable to represent say 'a third' in a decimal sense correctly so we use the recurring notation. In in this instance 0.33r *3 would be the same as 1, purely based on a flaw in the system... or perhaps not a flaw, just a side effect.
We could get around this issue by using a different base (instead of base 10), but at some point we will arrive at issue's like this with other bases.
This is the reasons why we have different types of math (such as fractions), so we can represent these figures accurately, and so they are understood correctly.
So... is 0.99r the same as 1? Yes. But only because we are unable represent certain figures correctly.