Honestly I would trade him for two reasons. One the team is in a terrible market so outside of them winning a title which they are not built for IMO Durant has no reason to stay. The second is by trading Durant your giving the team to Westbrook. That might not make him stay either but at least you can gauge how he reacts and go from there.
A healthy Durant is similar to Lebron he gives almost any team a chance to contend. Is there fair value for him no but if you can swing him for 1 young stud and several picks it's something you have to consider. A deal with Washington could net 3 1sts and 5 years of Bradley Beal that won't be equal value but Beal is a young stud and you get 3 chances to find gold through the draft.
You can essentially do the same thing next season with Westbrook if it looks like he is leaving. Move him for Russel, Randle and picks. You won't be close to contention for a while but you will have a few good young players you control for several years. It is essentially the Oakland A's model for running a small market basketball team.
Additionally, making those moves allows you to make more. Serge Ibaka could be dealt as well bringing in more assets. Now you are looking at 7 or 8 extra picks plus going so young the team is likely to get a high lottery pick, they got Harden, Durant and Westbrook from the draft it is not a stretch that within the 5 year window you control Beal for that they could find another all-star level talent with 12-13 first round picks.
Basically this is the Thunders window to win a title I would suggest that anything less that a competitive loss in the NBA finals and Durant leaves. That is a massive gamble for a team like OKC to take. I bet they roll the dice though and Durant leaves for nothing and then next season they deal Westbrook before he leaves.
I can understand your reasoning, and I appreciate that you're at least being consistent; but I have a different take. Your entire assessment is based on the assumption that the player is always going to leave for greener pastures no matter what, and IMO that reasoning is flawed. My take is that Durant probably really will only consider winning, and whether he is on a team that feels like it is giving him his best chance to win or not. If he feels OKC provides him a better opportunity to win a championship than anywhere else, he will choose to stay in OKC. If not, he will go to another team that presents him an opportunity that he feels gives him a better chance to win.
Certainly it's the ultimate gamble for OKC, but if not now, when should they gamble? They have a legitimate shot at winning it all, and they also certainly have some scary odds that they lose the second best player in the NBA for nothing. Certainly it's risky, but c'mon, you're seriously going to trade a pretty solid chance of winning a title next season simply because you're afraid you may lose him at the end of the season? I thought the goal was to win a championship, and in order to do that you have to take some risk. Pat Riley has shown he's willing to do this time and time again, and in his case it has resulted in multiple championships. Multiple times it has come crumbling down around him too, but he rebuilds, reloads, takes risks, and sometimes it blows up in his face, but other times it results in something pretty spectacular. The one consistent thing Riley does is he always leaves his rosters with a lot of salary flexibility, and guess what Olshey has done? Exactly that.
Personally I felt the same way with LMA's situation as I do with Durant's, and I am still of the opinion that if the Blazers had been able to be more successful last season he would have stayed. Unfortunately I think LMA's lack of killer instinct became a self fulfilling prophecy, as instead of hunkering down and fighting harder he instead became more and more dispirited with the team as a result of their lack of success.
I could see the chemistry from the 2014 team was unraveling on the 2015 team due to their lack of success after Wes went down. It's kind of sad but I think he, just as I, had thought that the team was legitimately only a few pieces away from really competing which is why he infamously stated he wanted to be the best Blazer of all time. But as many other posters have pointed out, the season disintegrated due to injuries to Lopez, Wes, AA, Batum, and even himself, and as a result everything came crumbling down.
The strongest bit of evidence I have to support my opinion is simply that LMA could have simply chosen to quit on the team with his wrist injury and no one would have blamed him. He could have quit on the team, got the surgery, then bailed for the Spurs just the same. Instead he opted not to do that, and in fact said he was doing so because he believed the team had the potential to make a big run this year. The fact that it didn't, and that we got so humiliated in the playoffs I think was really the deciding factor for him.
Sucks to be sure, but I personally don't hold it against Olshey at all. In fact I look at it the completely other way around and I admire his courage to stick to his guns and ride out the wave to completion. Certainly it blew up in his face, but much like Riley he will rebuild, create a lot of flexibility, and continue on with a new vision and strike when the opportunity presents itself. Plus with PA constantly stating he is looking for that GM with "the iron gut", I am pretty sure he agrees with me.