So this may or may not apply to your situation but I'll share and maybe there is something of use.
DS9 had a lot of similarities and we've had a lot of "he smart but..." conversations over the years. At 4/5 he was almost always the last kid out of the school and the slowest getting dressed (and we're in Canada so snowpants, jackets, mitts, boots, neck warmer and toques are needed for much of the school year which just adds to the fun). He drove us nuts and he drove teachers nuts.
When he was tiny daycare drop-offs were a nightmare and this continued into school. He developed complex rituals as a coping mechanism I believe. Transitions and the unknown cause stress for him so having a known ritual was comforting. It was a long sequence of different handshakes, fist bumps, hugs, kisses, certain phrases and if you missed one or didn't say the exact phrase right or did something out of order you had to start over. We were quite the sight in the school yard each morning.
For us another contributing factor (I believe) is that our DS has pretty low working memory (58%ile) and even lower processing speed (13%ile). These two things together combine for him so that when the teacher says "ok kids, the day is done, don't forget your homework, put your chairs and indoor shoes on top of your desk because they are cleaning the floors, go get your stuff on and line up at the door, oh and don't forget that tomorrow is crazy hair day" it just didn't work for him (although he is improving with age).
One of the biggest things that we changed at home was to simplify our instructions and give warnings to ease transitions (that last one we had figured out long ago on our own). He really needs time to switch gears and prepare for it. Then when it was time to go we'd do really simple, concise directions "DS snowpants", then "DS boots", etc. Breaking things down helped a lot for us. Eventually we started making them 2 steps, then 3, then 4... now we don't really think about it. If he is slower than usual then we resort back to the one step commands though.
FWIW DS had a lot of traits that resembled ADHD especially in school (that was what prompted us to test in the first place). The other piece of our DS's puzzle is an LD in written expression so in school some of his "not listening" was actually him just not being able to do the requested writing. The combination of LD/gifted is a hard one for teachers to process - most just don't get it.
We have tried to use natural consequences as much as possible. During school we just kept starting the whole process earlier and earlier so that there was enough time to accommodate his slowness. If he complained that he wanted more play time in the morning then we pointed out that we had to start early until we were faster. When he got faster then the natural reward was more playtime.
Not sure if any of that rings any bells or helps but I share your pain.
P.S. I loved the inconvenient troglodytes comment
