It has come to my attention that the timeline, particularly the times at which wielders belonging to different generations gained their keyblades, is not entirely clear. The goal of this submission is to answer any questions you all may have regarding the sequence of events and the chronology of keyblade acquisition, as well as to correct any past, future, or present time disparities on behalf of present and future members.
The first wielders began appearing (gaining their keyblades) shortly after Organization Nu was officially founded and began taking on its very first members. For the sake of this timeline I have placed this event at about two months after the start of ON. The first generation lasted about four months, which marks the "end" of the first generation - that is, no keybladers who gained their keyblades after this are considered members of the first generation any more.
The second generation of wielders began gaining their keyblades a short while after that, approximately two months after the last known first gen'er gained their keyblade. During the two months between generations no keyblades were matched to anyone. The second generation lasted about ten months and the last known second gen keyblader received their keyblade about three and a half months before the first third gen'ers began receiving their keyblades.
The third generation first began receiving their keyblades about three and a half months after the last known second gen'ers received theirs. This was about two months before the present time, marked as "Year 2" on the keyblade/ON calendar.
Jim founded his school, the Keyblade Academy, some time after the first of the second gen keybladers started showing up, at about ten (10) months after Year 0 on the timeline linked below. It has been in operational order for about nine (9) months currently.
I hope that clears everything up for everyone, since it took me about an hour and a half to put all of that together, including the timeline. It is missing a few small things and some of the colours are slightly askew, but everything that isn't covered there is covered above, so it should be fine for now.
Any questions regarding the timeline may be asked here if all the info above was for some reason unclear!