Training an entire starting 5 is not only ambitious, but long and painful for your team.
However, I'll not hide that I'm about to head in a similar direction. I'm currently holding onto a playoff position in my division and I feel that my team is good enough to take down any of my opponent (except for choo-choo who will be gone next season). I find it boring: for most of my last games, I didn't even both checking my opponents strategies. I'm confident that nobody can take down the current team I have if I play LI/M2M. Thus the only management I do is setting the enthusiasm for each game. In addition, I have maximum 2 seasons of "real" training ahead of me before I switch to stamina and free throws.
On the other hand, I feel the core I have now is good enough to make it to the ABBL but in the long run there is no way I'll compete with the top 5-6 teams up there.
It's probably the best time to sell for me now (market looks good and my players are young enough). I thought about it for some time and I'm now going for it! I like the challenge.
Back on the topic, I think it's not worth training the 5 starting players. You'd better train the key player that will be a game changer for your team. He'll be the "special one", the one you can't buy on the TL.
Then you can start thinking about the most interesting part of the challenge: how to shape your team while training this guy?
There are a few factors to take into consideration: back up players are very expensive while you could buy some highly paid balanced superstars for the same price.
Personnally, I thought about starting with a SF. I do not rely on the draft because of the X factor (aggressivity of the player: it's impossible to train and feature an extremely foul prone player in your starting 5). Therefore I'd first look for a 19yo consistent player who has been well trained during his first season. I'd train him with the future back up SF (just as young, but lower potential and starting skills so cheaper) and the future back up C. Single position training.
Once I'm done with the inside training, start the outside training for a few seasons with the 2 SF and future starting PG. That leaves me with 4 long term players. 4 to go to complete my ideal 8 men rotation.
After the single position training for outside boys, switch to double position: add the future back up guard on your roster + future starting PF (young) and future starting SG (should be almost finished - SGs tend to be cheap these days). Include these into the training rotation.
Finally, add the final piece (starting C). RB training for the big men + small forwards (last step). Then I could work with the bigs with a very reliable back court.
I imagine it could look like a cooking book. I'm aware this is a long, difficult and expensive plan. I believe in it and I know it's never gonna be as good as I expect it to be. I just find it exciting enough to give it a go.
After spending a few seasons managing a team, I have a better understanding of the game engine and the value of timing with trainees.
This example works for my project (which is not gonna happen if I can't sell my players at a decent price). The key points for me would be the following: timing, team shape (for the future strategy).
All of this can sound totally stupid. I may have missed something in this game. But hope makes you live and this is why we all carry on managing in BB.
I hope you enjoyed this wonderful wall text.
G'day all!
PS: forgive the spelling / syntax mistakes and the eventual offenses to anybody, I do not have the courage to read it again! =D