Oh man, this topic is killing me as well... So maybe someone of the more experienced players can give me a little help with their opinion to my SFs: 
I´m training outside skills and i have 3 of them, and i´m really not to sure how to train them exactly and how long i can go on. Rigth now i´m switching between JS, OD, and 1-2 times a season Driving (my SG need that).
Thats how they look like:
 Lin Mingcai (9261830)
Shooting Guard
Weekly salary: $ 7 245
DMI: 45000
Age: 20
Height: 6'0" / 183 cm
Potential: star
Game Shape: strong
	
Jump Shot: proficient 	Jump Range: proficient
Outside Def.: strong 	Handling: strong
Driving: inept 	                 Passing: mediocre
Inside Shot: strong 	Inside Def.: respectable
Rebounding: awful 	        Shot Blocking: atrocious
Stamina: strong 	       Free Throw: average
 Hansrolf Gruse (5769412)
Power Forward
Weekly salary: $ 23 399
DMI: 237400
Age: 22
Height: 6'1" / 185 cm
Potential: MVP
Game Shape: proficient
	
Jump Shot: proficient 	Jump Range: respectable
Outside Def.: mediocre 	Handling: awful
Driving: strong 	       Passing: respectable
Inside Shot: prolific 	Inside Def.: sensational
Rebounding: strong 	Shot Blocking: strong
Stamina: average          	Free Throw: inept
biratan Martim (5685996)
Power Forward
Weekly salary: $ 26 215
DMI: 112500
Age: 22
Height: 6'6" / 198 cm
Potential: allstar
Game Shape: strong
	
Jump Shot: strong           	Jump Range: awful
Outside Def.: respectable 	Handling: strong
Driving: proficient             	Passing: mediocre
Inside Shot: prominent    	Inside Def.: sensational
Rebounding: prominent 	       Shot Blocking: average
Stamina: average 	               Free Throw: awful
Tey all need different training, this Martim is pretty nice but already 22 and pretty tall, Gruse is small and allstar but hast weak OD and HN - wow, what can i do?
I would single position train OD (i know tough but rewarding) all of them... top guy will become a top SG (doesnt have RB) and the 3rd guy is a bit old so the sooner the better with him... middle guy with a bit of luck will become a BEAST.
Nice dilemma.. just discipline yourself training wise and if it means sacrificing a few games along the way I'd do it.... if you can get them all up 5 levels of OD you should be unstoppable relative to your competition.
I would not waste any time training Jump Range... it ill go up a little bit with normal JS training and the guy that should become your long term SG is already proficient... 1 more pop there should be more than enough..
OD first, second and third.. then worry about the other skills!