I fear that my lack of patience will be the downfall of the plan, as I only made it 2 cycles in my outside program before switching to inside. I was paying for a youth trainer for the first 2 years of a cycle, but given the fact that it's only for 1 player, it doesn't quite seem worth it, I'd agree with you there.
I bought Dowling as a 18 year old for ~75k and he had 31/20 skill points. I only trained him till the end of his 23 year old season, but in those six seasons I got 40 guard skill pops (only 10 between HA and DV) and 12 big skill pops (which I realize is just mediocre). I would guess if I had trained him another 3 years he would end up around 81/35.
The goal is to have a constant stream of players with manageable salaries that let me still be competitive every season. While at the same time, since I'm buy players fairly cheap, I am still making a decent profit every 3 years when I sell a player that ages out from my team. It worked great in D III, but it's starting to look like the ceiling might be a competitive D II team. It definitely does not seem like it will be sustainable in D I.