I wish more people felt this way. The OP gets it. It's not about "trolling" it's about the big picture. Would you rather watch the Celtics turn into the Knicks or would you rather them turn into the Thunder? One is a contender every year and the other battles for 4-8 seeds yearly.
You couldn't have picked a worse example. The Knicks have done the exact opposite as we've done. They have traded away their future for their current mediocrity. They gave up Jeremy Lin for Felton. Their management is terrible. Even despite being one of the most prominent big market teams in the league, Dolan screwed it all up.
Other examples of bad business? The Hawks before this year. The Bucks before this year. They achieved perennial mediocrity by, again, trading away young players for players that are not game changers.
On the other hand, to be OKC you would have to be bad not for just this year. You would have to be bad for multiple years to be in the lottery for multiple years. You have to hope that the lottery won't screw you over.
OKC was not only smart, they were also incredibly lucky.
Your "big picture" thinking seems to be that we put all our hopes into ONE lottery pick.
Meanwhile, Ainge has been stockpiling picks and maintaining flexibility.
Is there value in winning? Ainge is developing players. He's fielding a team that looks half decent and thereby driving up the value of his players (getting picks, potentially another first, out of the deal). He's allowing his coach to gain experience with a half decent team.
The payoff of tanking could be great. But the expected value is far less when you consider that: it's a lottery, there are busts, there are players who could be very good but not good enough.