Here goes an approximation.
We have $N=100$ strings of variable lengths, uniformly distributed in $1\cdots N$. Let $k_m$ be the number of strings of length $m$. We have $C^m$ ($C=256$) distinct strings, all equiprobable. And the probability of no collisions inside this set (given $k_m$) is , from the Birthday problem:
$$p_m = \frac{C^m !}{C^{m k_m} (C^m-k_m)!}$$
for $k_m < C^m$.
But $k_m$ is a random variable, and further $k_i, k_j$ are not independent ($\sum k_i = N$). We know, however, that $E(k_m)=1$. Lets introduce the approximation ("poissonization") of considering the $k_m$ as iid Poisson variables, so
$$P(k_m=k) = e^{-1} \frac{1}{k!}$$
Then the probability of no collision in the set $m$ is
$$ p_m \approx \sum_{k=0}^{C^m} e^{-1} \frac{1}{C^{m k}} {C^m \choose k} = e^{-1} \left(1 + \frac{1}{C^m}\right)^{C^m} $$
and the global probability is the product of the above for $m=1\cdots N$. In practice, only the first few terms have influence. One can even approximate further taking the first term only so that
$$p \approx e^{-1} (1 + 1/C)^{C} = 0.998052$$
or take logarithms and approximate even further:
$$\log(p) \approx - \frac{1}{2 C} = -\frac{1}{512} $$