I'm not sure if it's worth it to train OD to legendary. OD abd JR would train really slow for Rickard. I would train driving, passing and JS. It's always good to have high passing. High passing especially helps in tactics like motion and even low post to a lesser extent. I would give him at least two pops in PA and DR, then pump up JS and if you really want to OD.
Your second guy cannot be a SG because he has really low JR. Training passing would be good here since his is low. The driving training should give him training in handling also which should be quite a bit higher for a PG.
Seriously though, their JR is really low and should trained up if possible especially for the second player. The first could do with one pop in JR.
Your training has been pretty good so far and your judgement seems to be quite good.