Again, I'm aware these are real people behind the screen. This is talking mostly about their SMP characters. This essentially takes place when nobody is in prison (ahem ahem) and there aren't really any terrible things happening like a huge war.
Tubbo: He's around a toddler age-wise, but not in his terrible twos. He's quiet and nice and a bit shy, but when he gets excited and hyper you'll know immediately. Best friends with Tommy (almost like brothers) and Ranboo. He absolutely loves bees and his favourite food in headspace is oatmeal with honey and nuts.
Tommyinnit: He's closer to being in the terrible twos, but not really. He doesn't throw too many tantrums over "ridiculous" things like water being too wet, but it happens every once in a while if he's stressed. He's also super hyper. Best friends with Tubbo (again, they're like brothers).
Technoblade: He regresses to a super young age, but not too many people know about it. Only Phil knows, and that's because he's one of the only people Techno trusts. His headspace is around an infant age, at most two years old.
Wilbur: Usually big, and can caregive, but regresses every once in a while. He goes down to a toddler, but doesn't really have anything besides a few stuffies and a sippy cup. When caregiving, he likes to spoil the little he's taking care of, either with snuggles or stuffies or other treats.
Ph1LzA: Phil is a daddy, and tends to caregive whether someone is a Little or not. He's very gentle and kind, but he does dish out punishments and stern talking-to's if you earned one. He generally knows everyone's "status."
Dream: Can't see him as a regressor, but he takes care of George and Bad.
George: Usually big, but sometimes goes down to around five years old, sometimes older. He tends to stay by someone when little, usually Dream or Sapnap, because it helps him feel safe.
Sapnap: Maybe a babysitter type caregiver? Not a full time daddy, and I also can't see him as a regressor, but I feel like he's def there for his friends when they're small.
Badboyhalo: Gosh he smol. He's got a very wide age range, from almost newborn to almost ten years old. His age depends on how long it's been since he's been little, how stressed he is, that sort of thing. He also caregives, he's nice but makes sure littles stick to their rules.
Skeppy: Usually a caregiver, but sometimes slips down. He doesn't regress ever, just age dreams (I'll explain what that is if needed) and uses that to relax if he's stressed. He's more of a fun uncle type of caregiver.
Antfrost: Soft smol boiyo, he loves cats (of course) and soft, fluffy clothes and bedding. His littlespace is from baby to toddler. His favourite colour is a pastel blue. He's very sweet and quiet and shy, nobody really knows except Phil and Velvet (not mentioned in this chapter, I don't know much about him).
Eret: Not really involved in anything related to this, as far as I can think. He's okay with Littles but doesn't typically hang around them while they're in headspace. Someone said he should be a sort of uncle (in the comments, hi lol), so I'll say he comes around every once in a while with sugary treats for the littles, and then leaves hyper littles for the caregivers >:)
Ranboo: Really quiet and shy when little, has a relatively wide range (from around three years old to about ten). Normally sticks around Techno and Phil, and if they're not available he'll either be by Tubbo or on his own. When Tubbo regresses and Ranboo is still big, he'll take care of him. His nickname is "Boo" and he calls Tubbo "Bee," because that's just adorable.