Just a few thoughts to add on this interesting thread...
One of my instincts says that each Pluto generation, whether it fits chronologically with the definition of a generation (a little over one Saturn cycle) or not, usually does not figure out who it is until at least half of that generation has gone through its first Saturn returns and has the ability to see themselves in society and society within themselves. There is a maturity factor here that unlocks the unconscious operation of Uranus, Neptune and Pluto because one is ready to start looking consciously at their connection to the cosmos, whether it is globally (Uranus), trans-time and trans-space (Neptune) and the unknown (Pluto). Humans might be at their physical prowess at 18 or 19 (or at least we'd like to think so

), but there is still a lot of childhood in them. At the first Saturn return we are forced to face our own mortality and admit that we have a finite measure of time to do the incarnational work we are supposed to be doing. Uranus, Neptune and Pluto then can step in at a more conscious level and do their work more openly because they are the planets that allow us to explore beyond societal and familial conventions.
This being said, I do believe that there are some members of the Pluto in Leo generation who have managed to put off the lessons of their first Saturn return until their second Saturn return. Here in the US, I think this is why you overtly see the emphasis on the "culture of being young" so much. The Pluto in Leo generation here in the States blew up all the shots, the operations, the maskings of age into a multi-billion dollar business and made it be a crime to look ones age.
For the members in the US: think of the 50 year old grandmother with the Bowflex body and you will see what I mean—BTW, did they use Botox on the wrinkles on her face and dyed her hair so she wouldn't look 50?
Now I am not saying that the Pluto in Leo generation hasn't done this in other cultural settings because it probably has. It just might not be so "in your face" as it is here in the States. Part of that is because the US is still, I believe, in its late adolescence stage of development. The US psyche still believes that old teenage adage that "I know everything and I will never die." That, combined with Pluto in Leo, can be a dangerous combination, as we have seen in the last five years.
My high school class of 1976 had the last Pluto retrograde foray into Leo. So although I am a Pluto in Virgo generation person, I do see the schizophrenia that two year switchover can cause between the generations. Now each and every generation has its own form of rebellion and "anti-society" behavoir because that is part of the separation and individuation process of the person from the family to become an adult. Sometimes one does not realize the rebellion until some time has elapsed (and most of the generation has gone through the first Saturn return).
I think the biggest rebellers may be found in that group of the sign transition period because they really don't know if they are coming or going, so to speak. For myself, I know there are times that I exhibit Pluto in Virgo traits and sometimes I exhibit Pluto in Leo traits because I was socialized with both during high school. So I can alternately be amused (Pluto in Leo) and repulsed (Pluto in Virgo) by the antics of my age group.
This does not mean that there aren't other rebellers throughout each sign because there are. I just think they are quieter about the rebellion than the ones of the sign transition period.
What interests me is if the sign transition period expands dependent on how long Pluto remains in a sign. For the Leo through Scorpio generations I think the sign transition period averages about two years because Pluto stays in them the shortest amount of time. Sort of a Campbell's condensed cream of generation soup. As Pluto's orbit moves further away from the earth, the time spent in a sign lengthens to the point of being about a true generation or, to keep the analogy going, a pot of homemade soup. As Pluto gradually lengthens it stay in a sign, we may see things move at a slower pace, and the transition periods between signs maybe going to three or four years. I am only guessing on this.
The Campbell's condensed cream of generation soup gang wants everything fast-faster-fastest because they may fear "death" (i.e. change) the most. I think this is an artifact of the unconscious realization that generational time has been squeezed into a abnormal timeframe for human life. This is why the birth of the youth culture as we know it in the US may have happened in the way it did with the Pluto in Leo generation.
My 2¢ worth. Take what fits and ditch the rest.