Alright, very interesting. R I'm trying to mull over myself. I think since the other two have covered two versions of Leonard so well, the age angle is the best. Only question is which. If we want to ensure the potential girlfriend thing remains he could become only a year or two older than Ronald-- senior to him with that inherent dynamic, but still a high schooler. Or, if we wanted to take a page from the harem stories we're riffing off, he could be aged up into a 'hot teacher/milf' sort of char. Obviously in this case Leonard's new self couldn't be too interested in Ronald without drawing some jail time, but the vaguely alluring teacher could make for an interesting backdrop or catalyst for later parts of GC9R (particularly if Ronald has a class under her).
As for P, Glad you liked the jump there. Obviously that was a risk since Jon would conventionally be considered a late game change (and may well could still be for one of the other branches), but like you said opens up a lot of interesting possibilities. One thing I'm trying to figure out is what Jon could epitomize exactly. The P branch so far seems to take the candidates and make them into the most appealing version of their general role (Ranae is a forward, amazonian athlete, Laine is a cosplayer with a tendency to flaunt her amazing body). Jon, however, often is played as an 'average' guy. Or at least an average guy with some nerdy tendencies. So it will be interesting to see where we take him certainly.