you can only benefit from the off-season training once a week, so once you've successfully completed the training move on to the next person. i also don't think it matters how well you do (ie how quick, or hitting the red part of the target) in the training as long as you're successful.
also note that there are two 'parts' to each week in off-season, basically do your training and then play the friendly match, after which it will be 'negotiation round x', this is part of the same week so don't train again as it won't improve players at all.
regulate condition balances out the condition arrows. basically after 'regulate condition training' all your players will have atleast the 'middle green' arrow for form rather than some having down arrows...i'm not sure if it helps recover stamina or effect the little red bar that sometimes appears under players' stamina....i also think it sometimes brings down players whose condition is 'up red', so it may be a case of it takes the condition away from players with high condition to give it to those with low condition.
