Here's something I do:

To keep up with the daily bonuses, I train my whole squad with the easiest drills. This takes around 6% condition and when you tap the "x2" button you will get the double training bonus from the drills. (This doesn't affect how much your players will learn from the drills, only the Team Bonus acquisition)

And to keep up with the quality of my players throughout the season, I would separate my Defenders, Midfielders and Strikers in separate training groups when doing training sessions. Depending on the priority I've decided for the upcoming match, I would then decide how many time I would like to train each group, and would decide if I can nuke down some condition in order to do Very Hard and Hard drills or go with medium Drills just so they can get some %s in their Skills.

With me it all comes down to balancing out my club resources - How important is the next match? How many rests do I have left? How many Videos I got to watch today? Are my players keeping up with the training of other teams in my competition groups?

That's my play style. Would love to hear some other thoughts!