@GREENcar
Assuming everyone walks at the pace of the slowest person, you’d want the two fastest to act as shuttlers and the two slowest to only cross once, together. The huge time gap between the 1,2 min pair and the 99,100 pair does make the optimal strategy more intuitive here, and probably more pronounced with even larger group
Here are some of my other proposals: assume the fastest person can just carry everyone else on their back and then they can sprint across the bridge. Or assume Schrödinger’s principle applies and if we don’t observe them crossing, they’re both on and not on the other side, so the problem becomes trivial… Or if you’re in Middle Earth and everything else fails, just summon the eagles.
Before I come up with more silly ways, I think the general way to solve this is done quite well by modelling it as a graph and then applying a shortest path algorithm.