IMO FM2008 training has been tweaked so that attributes are less likely to improve / decline as frequently as in FM2007. Basically as you say, regardless of schedules, training has become slightly more time consuming than previously.
I find myself man-managing every single player (in training terms) in the squad (including the reserves and youth sides) either monthly or at the end of a 2-month period. This may sound daunting and boring, but believe me it is one of the very few effective ways of keeping tabs on player progression and development. Essentially, the more hands-on you are with training, the more rewards you are likely to witness as a result; once it becomes a routine to check training at the end of each month, you actually look forward to it tbh.
You must assess the attribute training graph to monitor for improvements frequently in order to decide whether a schedule is working for a particular type of player; his attititude towards the schedule is less important
IMO, because after all, you are the boss. Do this by using the training tab from the tree menu once a player's profile has been selected. Switch between players by using the two central arrows at the top of the screen. This is probably the fastest method because you can re-assign new schedules in one of the two training sections from the profile, as well as optional new positional training. Alternatively, right-click a player's name from the squad screen, highlight training schedule, then click a new schedule from the drop down list.