You need a "reserve". When you "borrow" you take one faith that there well be positive well at the end.
When you do the $-1\to 9$ you are borrowing $10$ and when you do the $-2\ 9 \to 8\ 9$ you are borrowing $100$ and so on.
And the final case when you get $8889$ you are borrowing $10000$ that.... just isn't there at all. So we have to do $8889 -10000 = -1111$. But thats an extra branch and takes us back to where we started.
But why go right to left rather than left to right? The reason we teach left to right to children is that in has the advantage we only have to keep one tally and "borrowing" or "carrying" won't require as second tally to keep track of. But note: we deal with the minutia first.
If we go right to left we deal with the highest powers of $10$ first and that's what's going to dominate the entire number.
If we go right to left and our first term is negative... well then then entire term is going to be negative, and if it is positive the entire term will be positive. Then we borrow and carry only when you change signs; making them all negative if the first term was, or all positive if the first term was.
So having $-1\ -1 \ -1 \ -1\to -1111$ is the corect answer.
Let's do a more complex issue $3649 +(-5493)$ will give us
3 6 4 9
-5 -4 -9 -3
-----------
-2 2 -5 6
-1 -8 -5 6
-1 -8 -4 -4
So $3649 + (-5493) = -1844$
And were we to have the other way $ (-3649)+5493$ where the positive is higher it works the same way.
-3 -6 -4 -9
5 4 9 3
-----------
2 -2 5 -6
1 8 5 -6
1 8 4 4
And $ (-3649)+5493=1844$