Muttered Thoughts About Team Construction and Relative Player Value

But the bottom line is that in general teams need multiple players to "outperform" their contracts to be championship contenders.
The problem with this building strategy is that there can only be five "Top Five" players at any given time, and while the number of these "supermax" players isn't fixed, it's sufficiently small that there are far fewer than one per team to go around. I'd suggest in today's NBA there are about six depending on what you think of Dirk Nowitzki and Tim Duncan at this stage of their careers, and then another group of about 12 who are outperforming "max" contracts but not but the enormous degree of the very top players. The value of "supermax" players is so well understand that acquiring one via trade is difficult if not impossible (with some the exception of impending free agents, but that's more of an extension of the free agency process.)
Similarly, adding these guys in free agency is out of the question for many teams by virtue of geography and market size. Further, the current collective bargaining agreement has rules in place incenvtizing these players to "stay home" and re-sign with their current teams in the form of additional years and money on contract extensions.
The fact that acquiring these players can be difficult leads teams to try and "grow their own" by drafting them. The natural extension of this is of course tanking. However, tanking and relying on the draft is a very low percentage play. I'm sure the teams who took that route are quietly disappointed in the way Andrew Wiggins, Jabari Parker and Julius Randle haven't lived up to the hype or that Marcus Smart has not progressed (speaking only of on-court topics. SuperFan incident says far more about SuperFan himself and the priorities of NCAA 'institutions' than it does about Smart).
So what then is a rebuilding team to do?
The short answer is it depends. There really is no "model" that provides much guidance beyond make "good decisions, hope they work out well and always leave yourself outs." Despite the relative lack of media, financial or geographical advantages, Indiana was able to recover from its mid-2000s doldrums much faster than were the Knicks because the Pacers understood that sometimes the best thing to do is simply stop digging.
At risk of this becoming too recursive, let me back up again. The above only applies to teams that are genuinely and to the exclusion of virtually anything else seeking championships. Hayward and Stephenson could easily be important additions to teams which are "tough outs" in the second round of the playoffs before bowing out to teams that simply have them out-talented.
It is a matter of picking the proper baseline for analysis. Is Gordon Hayward an above average starting wing in the NBA? Certainly. Would he be above average compared to the starting wings for playoff teams? Somewhere between maybe and probably. Would he be above average as compared to the starting wings on the 6 or so teams that have any real shot at the title? Absolutely not.
And herein lies the folly in paying him max money - you're using a great deal of all three of the four resources as team has at its disposal to build a contender: money, playing time and shots (the fourth being draft picks). And you're using the resources on a guy that has to go head to head against the best players on many of your opponents, but is a demonstrably worse use of all three. In other words, you're fighting the war on his turf, which is the surest way to earn a pat on the head and a photoshop with you on a boat next to Ernie, Kenny and a minor celebrity from your neck of the woods.