Let $P_{n}=\left(x_{n}, 0\right)$. Then the $\ell_{n}$ meet $\mathcal{C}$ at $\left(x_{n+1}, x_{n+1}-x_{n}\right)$. Since this point lies on the hyperbola, we have $\left(x_{n+1}-x_{n}\right)^{2}-x_{n+1}^{2}=1$. Rearranging this equation gives $$x_{n+1}=\frac{x_{n}^{2}-1}{2x_{n}}$$ Choose a $\theta_{0} \in(0, \pi)$ with $\cot \theta_{0}=x_{0}$, and define $\theta_{n}=2^{n} \theta_{0}$. Using the double-angle formula, we have $$\cot \theta_{n+1}=\cot \left(2 \theta_{n}\right)=\frac{\cot^{2} \theta_{n}-1}{2 \cot \theta_{n}}$$ It follows by induction that $x_{n}=\cot \theta_{n}$. Then, $P_{0}=P_{2008}$ corresponds to $\cot \theta_{0}=\cot \left(2^{2008} \theta_{0}\right)$ (assuming that $P_{0}$ is never at the origin, or equivalently, $2^{n} \theta$ is never an integer multiple of $\pi$ ). So, we need to find the number of $\theta_{0} \in(0, \pi)$ with the property that $2^{2008} \theta_{0}-\theta_{0}=k \pi$ for some integer $k$. We have $\theta_{0}=\frac{k \pi}{2^{2008}-1}$, so $k$ can be any integer between 1 and $2^{2008}-2$ inclusive (and note that since the denominator is odd, the sequence never terminates). It follows that the number of starting positions is $N=2^{2008}-2$. Finally, we need to compute the remainder when $N$ is divided by 2008. We have $2008=2^{3} \times 251$. Using Fermat's Little Theorem with 251, we get $2^{2008} \equiv\left(2^{250}\right)^{4} \cdot 256 \equiv 1^{4} \cdot 5=5(\bmod 251)$. So we have $N \equiv 3(\bmod 251)$ and $N \equiv-2(\bmod 8)$. Using Chinese Remainder Theorem, we get $N \equiv 254$ $(\bmod 2008)$.