((Disclaimer: I really don't know how prisons function in terms of medication and accommodations, but I don't really hear good things so that's where part of this is coming from.
Also, as per usual, I went overboard LOOOOL. Enjoy!
This is a very good question, and I think the answer to the first and second questions comes down to the recognition of such an integral person in the Stark household: Jarvis.
Oh yes, Jarvis is 100% still around in this AU, and why not? For the Stark home would run more amuck without him than it already was. While Charlie was away for work purposes, and Maria had all of her engagements and responsibilities as a Stark woman, the boys were in the care of Jarvis (and a nanny here and there but mainly Jarvis). And Jarvis learned very quickly that these two boys would not be ready on time for anything without a guiding hand to help them.
While Tony is more like his mother, he did inherit quite a few things from his father besides the last name, and one of those things was the enjoyment of little rebellions against Grandpa Howard Stark. The other was being naturally fashionably late. Which also became a little rebellion of sorts. Howard Stark was a stickler for being on time. Charlie was not. Howard was the “five minutes early is still late” kind of guy, and Charlie was the “five minutes late is still on time” kind of guy. Now if it was something pertaining to his wife, his kids, or something he enjoyed - things he deemed important - Charlie would move heaven and earth to be on time. Otherwise, Charlie was fashionably late by nature. Tony is also fashionably late by nature, unless he deems it of the utmost importance to be there on time.
Scott is not a fashionably late by nature kind of guy. He prefers to be on time when he can be, but he’s more of the “stumbling in or rushing in late while somehow managing to hold it all together” type. That’s mainly due to his ADHD. He’ll think of at least ten different things he needs to do before he leaves to go somewhere which will only take a second to do but in reality take ten minutes per thing. And each thing could potentially lead to at least two more things that he’s reminded of. This is also assuming he’s having a good day with his ADHD, and he didn’t forget he needed to leave in the first place. If he has to go somewhere he doesn’t care to go at all, well, it’s extra easy to give into those ADHD tendencies, if you know what I mean.
That’s where Jarvis comes in. Jarvis keeps the boys in line and on time. He is British, of course, so you can imagine how he prefers things in tip top shape. On an average day, Scott is easier to get out the door first because he prefers to be on time to things. Jarvis sometimes has to put more effort into getting Tony out the door unless Scott’s having a bad ADHD day. But since Jarvis was in charge of making sure Scott took his meds for a long time, that wasn’t a big issue.
As they got older though, these behaviors didn’t change; they just became more cemented.
For Tony, inheriting the Stark empire at such a young age and falling into Stane’s wicked grasp in the process further cemented Tony’s choice in what he deemed important. Fashionably late by nature also became fashionably late by choice. A statement. Anyone who understood him only had to pay attention to when he arrived at an event to see what he valued most. And as time carried on, how much he drank at said event to numb himself to the negative feelings pooling in his belly but that’s neither here nor there.
Then Afghanistan happened, and a lot of Tony’s choices were taken away from him, including when he showed up to the beck and call of his captors. If they summoned him, and he didn’t answer in a timely manner, they’d drag him out and teach him better time management. He quickly learned that to stay ahead of this game, fashionably late was not an option. It took him a long time after the fact to not let himself give into the panic that would swell in his chest when he had somewhere to be he didn’t want to be. Fear was a teaching tool too many people in his life liked to use, and he refused to bow to it in this part of his life too.
After he was rescued, fashionably late became a reminder that he is still human, still him, and he has the gift of choice.
For Scott, the struggle to be on time despite his ADHD tendencies became more apparent after losing his parents, losing Jarvis, and losing Tony to Stane and Stark Industries. Basically his whole support system. College was tough, not because of the classes but being on time. Once Maggie came into the picture, she helped him stay ahead of the game because was a woman of precision, and she helped him remember to take his meds. She was patient and understanding about all of that.
Prison was exceptionally challenging to him and his ADHD. The prison didn’t really care if he ran out of meds or not. The meds didn’t keep him alive, so they weren't a medical priority, even for a Stark. There were a few medical staff who liked him well enough to remember his meds for him when he ran out, so at least there was that. But he couldn’t keep them on his person or in his cell because others would steal them, and that fact caused its own problems. The prison didn’t really care if he was late to meals or curfew or fill in the blank either. You’re late? Tough luck, there’s consequences. He was on his own. Until Luis came into the picture as his celly and saw how Scotty without his meds really was. Luis helped keep him in line to go eat or to be back in the cell for lights out and things of that nature.
Once he was out of prison, it took a long time for Scott to break out of the mindset that if he wasn’t on time something bad would happen to him. Panic kept him on time but exhausted, and he hated feeling afraid of consequences that his anxious mind would fabricate. He never wanted to feel like that again.
After prison, rushing in and holding it all together somehow became a reminder that he was trying, he was doing better, and he was improving all the time. And if he didn’t get it right, that’s okay because he’s still human, and grace is a gift he would give when it was needed, including to himself.)) @loki-notazombie
