So because i was a bit of a jerk with my list of things to help tough win, heres my analysis of why i wouldn't do this at all.
1) Looking at his conference right now, he only really has one team that is front of him that has a lot of higher salary players (doesn't necessarily mean they are as good as their salaried worth, but i'll pretend that all of these guys are close to worth their salaries). That guy has a huge stadium, as is essentially on his way to being D.III again next season unless something unforseen happens as he can afford most if not all of the salary he is taking on. The second team in his conference has one really good center presumably, a good secondary center that players PF, two SG's (one that cant handle the ball to save his life that plays SG and the other that presumably has better handling that players the standard PG position). However, this guy has less arena, so he might not maintain that roster for too long even though most are young enough to carry him into D.III within two seasons. The next team in line has the arena to support a payroll, but has roughly 11 guys that are all above 5.5k salary. I think tough could easily slip into the 4th best team if he improved his depth to match this guy. No requirements at all to buy a lot of 40k guys within the next season or two. It will allow him to work on some of these younger guys and win enough to not ever play a relegation game to stay in the conference.
2) Looking more directly at tough, we can see a few guys that are good in terms of salary versus age as far as development goes, but we can see that their skills aren't all good. I'll make my point on a few players:
A - Vasko, the young PF. While he is overmatched in a lot of ways with some of the bigs in his conference and in his league in general (which tough himself wisely noted at a few different points), i can't imagine his handling or passing are that good. I don't see passing or handling needing to be over 4 to be at the D.IV winning level, and my guess is that Vasko is a true 1 at passing and maybe a 3 at best in handling. I'd spend the better part of a season trying to correct that if i were seriously training him.
B - Sol, the young center. Same sort of problems. I think tough was more interested in grabbing some other secondaries, and it hurts his teams ability to maintain possession.
In fact, just looking at team tough, it's not that great across the board. 184/77 is the TO/Steal ratio, 152/184 for the Assist/TO ratio. Not to toot my own horn in a weaker division, but my ratios are 111/80 in the TO/Steal ratio, and it's a 182/111 Assist/TO ratio. I did a quick search of the market for centers and forwards under 20 with inept handling and passing, and found about 5 within the next 12 hours, 3 of which are probably going to fall within 30-40k to get on the team, 1-2 that really fit the C or PF mold. He might not have the money right this second, but he should be capable of generating enough cash-flow with that the fans filling in roughly 7500 seats to grab a few more of the 5-8k guys that many of the 2nd or 3rd best teams in his conference and in his league overall. which was the point i think i made in an earlier post.
need a second post to cover the remaining points.