DIY Tubular Skylights for special application; seeking tubular skylights smaller than 10"
Your question is very complete. But, for a flat concrete roof? Yes, I know, it won't truly be flat and it better not be. Either way is No Way...you'll be re-caulking every year and it'll take all year long with that Swiss Cheese.

Please have the mason customize the roof for these. I'd like to see a 2" to 3" (twice that if you regularly get snow and ice) ramped cone poured for each location that's part of the initial monolithic pour...not some add-on guaranteed failure afterthought nonsense that actually collects and retains water.

Also, please don't run short-lived Romex under the slab for the night and cloudy lighting. Use the aluminum armored cable, unless it's attacked by the concrete. Then you might need the PVC or epoxy coated armoring.

I'd actually suggest a sidewall stovepipe looking singular tube that feeds a fiber optic lighting box. Of course, it could be a nice feature like a faux gable or corner turret. But, this would allow for experimentation and scalability. Maybe 4-inches is too bright in a fiber optic setup and you just need a 2" periscope that operates as a flagpole.