Let $c = \log_2 1000$. Then $f(x) = c\log_2(x+1) - \log_2(x+k)\log_2(x+1)$. Differentiating and equating to zero, we get
$$
\frac{c}{x+1} - \frac{\log_2(x+k)}{x+1} - \frac{\log_2(x+1)}{x+k} = 0
\implies c(x+k) = \log_2[(x+1)^{x+1}(x+k)^{x+k}]
$$
The RHS is a monotonically increasing, concave-up function. So, the graphs of $$y=c(x+k) \quad \text{ and } \quad y = \log_2[(x+1)^{x+1}(x+k)^{x+k}]$$ intersect at most once. We also have that $$\lim_{x \to 0^+} f(x) = 0 \quad \text{ and } \quad \lim_{x \to +\infty} f(x) = -\infty,$$ and that $f(1) > 0$ when $k$ is in the range you mentioned ($1 < k < 500$). Hence, there is at least one critical point of $f$. Thus, there is a unique critical point, which will be the point of maximum of the function. Hence, a maximum always exists.