Player 1's lack of jump shot is pretty painful, but seeing that the skillset of the group demands JS training, its manageable. Long-term, it'll hurt his value and could limit your training options but on the whole you have a trainable group.
As for skill rotation, I'll tell you my guard training plan:
3 weeks One on One (for HN, DV, JS)
3 weeks Pressure (OD)
3 weeks Passing (PS, HN, DV)
3 weeks Outside Shooting (JR, JS, HN, DV)
This way, I train all the important guard skills. You'll probably want to mix in some jump shot training this season or next in place of either One on One or Outside Shooting. Do not skimp on the defence and passing training.