Why is it that despite being kidnapped, going to be made into coats, and separated from their parents, the puppies didn't seem the least bit upset or scared while they were in Hell Hall with Jaspar and Horace?
Children adapt surprisingly well to situations they can't control, and as for the coats thing, it's no new thing for kids and teens to think they can't get seriously hurt. It can be easy for them to pretend danger isn't real until it's impossible to ignore (such as when they were actually being chased and they reacted with fear).
How did the dogs make it back to Roger and Anita in London without attracting attention at the sight of a colossal pack of dogs in one of the largest cities in the World?
Well, they'd thrown Cruella off the trail at that point, so nobody was looking for them. Plus they were hidden in the truck most of the way
Black dogs, dark night...it's plausible that no one would notice them if they kept to the shadows. Plus there is the implication that it is Christmas Eve. There probably wouldn't be too many people out and about, and if anyone had been and said, "I just saw a giant pack of black dogs! I think the grims are out to get us all," it would probably be dismissed as someone hitting the eggnog a bit too hard.
If you saw a pair of black dogs walking down the street with a large pack of puppies trailing after them, what would you do? You'd stop and stare for a moment, think "that's weird," and be on your way. There's no reason a passerby should particularly care, apart from the fact it's an odd sight.
Dalmatians' fur is rather short, and not particularly soft even in puppies. Plus, if the stories of dog-wool sweaters are to be believed, the "dog smell" doesn't go away. Why would anyone want to buy a coat like that? Or wear it in public, knowing the source is self-evident and would mark its wearer as a dog-hater?
Well, generally speaking, high-class fashion has often been more about flashiness than comfort. And as to wearing it in public, well, the idea of making a coat out of dogs is so absurd that it seems likely many people would just assume it's fake. Although that does kind of kill the point of showing it off...but then, one might assume that the sort of person who'd buy a coat made from dogs would spend most of their time around people who share their...uh...unusual preference.
In the original novel, Cruella actually bothers to address this factor- She plans to make the front side of her coat Dalmatian and the wrong side made of some other, less conspicuous fur. Until the fuss over the abducted puppies dies down, she was going to wear the coat Dalmatian inwards, and then turn the whole furry coat inside-out.
If Roger and Anita have such big financial problems that they apparently can scarcely afford to feed themselves, then why on earth do they have a Nanny?
In the book they each had a Nanny living with them before they were married (presumably the same nannies who had watched over them as children - Rodger's Nanny says at one point that she's been caring for him since the day he was born), and both Nannies continued to live with them after the wedding because they were more like family by that time than servants. It's safer to assume that movie!Nanny had also been with one of the two since childhood (probably Anita, given the state of Roger's flat when the movie starts) and remained with the new couple for the same reasons as in the book. Of course, they are also much wealthier in the book than they are in the movie - Roger is a successful financier, not a broke musician - and would have had no trouble being able to afford household servants.
Movie!Nanny does make an offhand remark about Anita's childhood artistic talents, and how happy she is to be there as she starts a family of her own.
Even in the movie Roger isn't exactly poor, he's successful enough at his craft to afford a dog and all his instruments, eventually buying a house. Cruella is most likely simply being mean when she says they can barely afford to feed themselves
Alright, so in the end, Cruella lost both all the puppies and her nice car...happy ending yet? She still has her money and she still has her mansion, I mean, she even knows Pongo and Perdita were leading the puppies home! She could easily get on their tracks again, knowing who owned Pongo and Perdita. She even lets herself into their own house! Can't hide those 101 Dalmatiansforever?
The end of the film and the sequel address this. The whole family moves to the countryside. Cruella was sent to prison, and after getting out has no idea where they've moved (she even tries going back to their old, empty flat and feels offended they didn't leave a forwarding address). She's given a restraining order, which requires her to stay away from the Radcliffes, animals, and furs. It's only because Patch accidentally got left behind during the move that she gets the farm adress. If not for that it's highly unlikely she would have found them.
Here's a big one to me. In the animated movie, one of 84 puppies indicates he was bought (presumably from owner or store). If Cruella already buying puppies, why bother to steal other 15 newborns from Roger and Anita?
There weren't any more dogs left to buy or steal?
It was an act of petty revenge against Roger and Anita (mostly Rodger) for actually standing up to her and initially refusing to sell the puppies.
Concerning Two-Tone in the TV series, why would the Dearlys have her ear pierced?
I guess they like earrings?
Maybe she did it behind their back. Don't know how, but still...
Anita is, by all appearances, a very kind person and animal lover, and not at all a fashionista, yet the way Cruella talks to her and the way Anita defends her to Roger seems to indicate a strong friendship. How in the world would this happen between such radically opposed personalities? It seems unlikely that they'd even run in any of the same social circles.
All the Disney-related continuities made after the film explained that she worked for Cruella's fashion company.
In the book, they went to school together.
Live-action movie and sequel
If Chloe doesn't believe in second chances, why is she working as a probation officer? And if she refused to believe that Cruella had changed, why does she instantly believe Kevin is guilty?
For the first point, perhaps she had become a probation officer with the belief in second chances? And then years of having to deal with rotten clients made her cynical and believe that it's impossible for criminals to reform. As for believing Kevin is guilty, the situation looked very much like he had taken her out to dinner in order to secure an alibi for himself. She was probably very offended and hurt that she had possibly been duped and lied to.