I attempted to answer that question. The biggest detriment is the CBA and one point I left out was the floor for salaries for each team. If a team does not spend the floor amount (this season $49M) the difference of the money is divided among the players. So theoretically a 20 win team with a payroll of $25M could see each player receive a bonus of nearly $2M at the end of the year.I think all of these observations are axioms, so the question is, why do so many teams refuse to do things this way?
I don't think your points above are in sync with the points I made. Regardless, I was merely trying to offer insights with the current system as to why I don't think teams do things the way you have described. To your points above:
1) I totally agree. Long term cap killing contracts are bad for every team. A shit team like Toronto has shown it to be a true and an elite/contending team like Cleveland with LBJ has shown it to be true.
2) I agree again. DeRozan's extension was beyond stupid given his skill set and the leverage Toronto held.
3) Disagreement here. Teams very rarely go from bottom feeders to championship winning or contending teams. THe 2008 Celtics come to mind, the Spurs with an injured David Robinson, and little else. Even the Miami Heat were a first round playoff team before the summer of 2010. I do not think it is realistic for teams to go from 20 wins to contending. There has to be a progression. Memphis showed this as did OKC and Indiana (using examples of recent teams who are contending). While you as a fan might not see much difference in a 20 win and 40 win team, I can guarantee you the majority of fans (ie. attendance) and sponsorship disagree. I respect your opinion but it covers a very narrow scope and is black and white.
4) Whether it is draft or free agency, your whole premise relies on getting superstar talent while having a roster of high value complimentary players on the cheap. It sounds good in theory but the practicality of it is bordering on impossible over the course of many seasons. Even San Antonio has had to pay middling talent much larger contracts than minimum: Richard Jefferson 4 years/$38M; Boris Diaw 2 years/$9M; Matt Bonner 4 years/$16M; Splitter 3 years/$12M. Jefferson flamed out, Diaw plays 16mpg in playoffs, Bonner plays 14mpg and does not meet the criteria you've laid out, Splitter took half his contract (1.5years) to become a valuable piece.
5) Cleveland is an awesome example of what not to do with a superstar, no question. They blew their cap space on a shit player and then had to keep rolling that contract over for other shit/overpaid players - much like the sequence of events for Colangelo with JO to Marion to Turk to Barbosa.
6) This ignores the situation Toronto eventually found themselves in with Bosh. A team is not going to give up valuable assets for a player who could bolt in free agency and is unwilling to sign an extension. Once a player refuses to sign an extension (and the new CBA rules make it in the players best interest to NOT sign an extension but to hit unrestricted free agency) you are over the barrel when it comes to negotiating. This situation also ignores the cap holds in the current CBA and the ability to sign players once over the cap. You can't sign free agents without renouncing your own free agents or cap holds. As your example implies, once you sign your superstar player and you go looking for more to pair with him you then only have minimum contracts to round out your roster. There is little to no hope of continuity or building which is one of the pillars of the San Antonio organization. At some point you are going to need to pay these middling cap killing contracts.
7) I don't think your system would have allowed Green to sign a 3 year, $12M contract.
8) This is where I am finding a lot of contradiction. You ask why teams don't run in the manner you describe but then ignore the realities of the CBA. You are correct though: the CBA is what it is. Whether you would do away with it and other things or not is not the issue. The issue is why don't teams operate in the manner you describe, and I would add, within the parameters of the current CBA.
9) One year ago no other team would have got Marc Gasol because he was a restricted free agent. Having the cap space is great but what good is it if you can't get players you want or add value. It will be very interesting to see what happens with Houston this summer in their pursuit of Howard... although I find this a bit puzzling considering they already have a C who creates an above average impact on the court getting paid 60% less than what Howard would make.
10) Hibbert is a max contract?
He averaged 11.9 ppg on 45% shooting (has never shot over 50%, struggles earlier this year due to contract expectations, 47% for career) and 74% from the line.
Your premise began with there only being 30 guys in the league worth big money. This list has 24 players and Hibbert comes in at 23 for WP/48mins. Just on NBA C's with your assertion that Hibbert is an NBA max worthy player, based on simple and advanced statistics one could make the argument that every NBA C who is slightly better than average is a max player candidate.
11) I am in agreement here. I give a little more leeway for bigs. However, even San Antonio pay for potential. They did it with Green and they did it with Splitter. Toronto did it with Bargnani and it back fired; did it with Johnson and it paid off; and did it with DeRozan and I expect results closer to Bargnani. The difference between SA and TOR, of course, is the amount of dollars involved and with that I again am in agreement with you.
I talked a little about San Antonio in the post. I 100% disagree on Dallas though. Before Cuban broke up his championship team he was one of the most prolific and irresponsible spenders in the league. Whether it was through free agency or trades, he had some awful, awful contracts go through his roster. Diop, Haywood, Carroll, Najera, Tim Thomas, Dampier, Josh Howard (which is a good example of how a productive player can turn in to an unproductive) are off the top of my head.