Find optimal number of videoclips to watch (depending on length) to get Maximum points.
I will assume the supply of videos is unlimited and each video is worth 1 point (limited supply would make the problem significantly harder).
We want to maximize the points earned per unit time. It is easier to (equivalently) minimize the time needed to earn a point. Since this is random, we will minimize the expected time needed to earn a point. Our strategy would be to watch all videos that are no longer than some maximum time $m$.
So, if we know $m$, what is the time needed to earn a point? First, we have to wait 5s for each video that we get longer than $m$. Then, we need to watch the video that we get that is shorter than $m$.
The probability to get a long video (and thus skip it) can be calculated from the histogram. Lets call that $p_m$. Then, the number of videos we will skip follows a negative binomial distribution with $r=1$ and probability $p_m$. The expected number of skips is thus $\frac{p_m}{1-p_m}$.
Similarly, from the histogram we can compute the expected video length given it is at most $m$.
Thus, if $L$ denoted video length, our time spent per point is $T(m) = 5\sec\frac{p_m}{1-p_m} + \mathbb{E}[L | L \leq m]$.
Now we want to minimize $T(m)$. We can compute it using our histogram if given $m$. While we don't have a closed form expression, we only have a single parameter, $m$, that takes values between 0 and 1000, so it shouldn't be hard to optimize, we can use a simple grid search to find the best $m$.
Extra note: There could be an alternative formulation, where instead of maximizing the points earned per unit time, we have a hard time limit for watching videos and want to maximize the total score. If the time limit is large, the above is a good approximation. But for a small time limit, the problem becomes significantly harder. In that case, the optimal threshold might change with time remaining. We can try to tackle that case by defining two functions $S(t)$, which gives the optimal expected score if we have time $t$, and $m(t)$, the video length threshold as a function of time. Then we have, $S(t) = S(t-5)\mathbb{P}[L>m(t)] + \mathbb{E}[S(t-L) + 1|L\leq m(t)]\mathbb{P}[L\leq m(t)]$. We can then use dynamic programming to find $m(t)$ and $S(t)$.
Addendum: Note that the above assumes that the 5s wait happens only if we skip a video without watching it. Since in fact the 5s delay happens even after we watc ha video, I added 5s to the length of each video.
The above can easily be implemented in python:
times = open('times').readlines()
times = [int(x)+5 for x in times]
def pm(m): return len([x for x in times if x > m]) / len(times) # this computes p_m
def em(m): return np.mean([x for x in times if x <= m]) # This is E[l|l<=m]
def t(m): return 5 * pm(m) / (1 - pm(m)) + em(m)
min(range(min(times), max(times)), key = lambda x:t(x))
The minimum $T$ turns out to be at 54 seconds. Note that this is after adding 5s to the length that I mentioned above, so the answer is 49 seconds.
Note that while 49 seconds technically gives the optimum, all cutoff values between 48 and 53 have pretty much the same scores.