The conclusion that the training project came to is that JR doesn't speed up OD but OD slows down JR. I am a little skeptical about that finding but its the best data we have.
I would probably do 1v1 first just because you can train up to 5-6 guys. Keep the best three trainees and go to single position training: JR-> OD/PA -> and then JS but you could really put JS anywhere after 1v1 if you have to I just value getting OD on my guards as quick as possible for competitive reasons.
Once again it probably makes sense to do something like IS-> ID/SB -> RB so that you are doing all your single position training in a row.