I don't like Gilbert. I think he has made plenty of bad calls, but I think the most important thing is his checkbook, and he has never been cheap. LIke you say, he also understands the fan base especially being form Detroit, he gets the vibe. He would never sell the city out like that, so he does have a sense of loyalty even when he is misguided.
I know people have said he "lied to the vets" etc etc. But really, he just sent Korver to a place he loves, he got George Hill to a place where he can compete, and could be a threat to any team in the league come playoffs. There is even talk of doing right by JR, who absolutely deserves it for 2016, and also absolutely deserves nothing due to the distraction and bad teammate he has been this year.
A meddlesome owner is annoying AF, but he has not drawn the line at some outrageous roster prices and he has to be given credit for doing everything he can to win. He's willing to go to the mat, even if he doesn't always make the best decisions when he gets there.
If we had OKC's ownership or the Suns for instance we would not have even one chip. Yeah I'd rather have the Spurs org, the Warriors or even the Mavs, but I;'d also like to have Kawhi than Clarkson lol and Pop over Drew.