I agree with superfly. It is not efficient at all to switch between one and two position training at all. You either lose a lot of training age of other trainees who get no training during one position training, or you would train non-trainees while doing two position training.
I'd recommend to train him at all guard skills for one position training first, which would be OD, HA and PA. By training handling you train driving almost at the same amount due to its sub-training effect. After he reaches decent skills in these categories I would switch to two position training, training JS and DR and add some more trainees of course. Maybe after one or two or three seasons, depending how strong you want him to be at OD, HA and PA.