I never saw that much tactical group/raid planning. Like most of the older players, characters were made here and there, and flagged in the same fashion. And then there were the people you played with, who did the same, and then you help them. So yeah it's a real thing to go through it more times than you are willing to keep track of. What some might consider proper thoughts and planning on character management are not reality in practice.
I think the meat and potatoes of this entire issue is that there was a split, when we used to have to work with others to now when we are all alone by ourselves. I don't see choke points that remain as a "challenge", but rather broken remnants of encounters not revisited to the new way we have to play. I mean when was the last time Lithluran was killed by anyone? To make matters worse, some content in the latter days is indeed put out that is best suited for individuals playing individual characters in a group with others. Things like that make me question if anyone writing this stuff even knows what they are doing. Not in a competence matter, as in you know how to code, but more along the lines of are you even aware of what this place did to itself that you can't see there aren't even a total of six people playing to operate these things as intended?
Flip or flop, but don't flip-flop.