One serious and one less serious solution
(1) If one says that a series is divergent then the one has to define in what sense it diverges. The norm referred to by the answerers above was the absolute value of the integers in question. There are other norms over the field of rationals. We are going to examine the convergence problem at stake assuming the so called $2$-adic norm. (see: http://en.wikipedia.org/wiki/P-adic_number)
Every rational $q$ can be uniquely written as $$q=2^{\ r}\frac{m}{n},$$
where $m,n$ are relative primes and $2$ does not divide either of them. The so called $2$-adic norm of $q$ is then, by definition, $$|q|_2=2^{-r}.$$
(Show that this is a norm...) Now
$$\lim_{n\rightarrow \infty}|\sum_{i=0}^n2^{\ i }-(-1)|_2=lim_{n\rightarrow \infty}\ 2^{-(n+1)}=0.$$ That is, we have a convergent series.
(2) In two's complement notation $1111...111$ means $-1$. One meaning of this sequence is the series above and the other meaning is $-1$ and this is independent from the number of digits we use.