Her friendship with Anita is well-established, but Roger is barely in the movie and I can't recall any scenes where he and Cruella said three words to each other, let alone became close enough that she would gift him with a puppy at the end.
They both worked closely with the Baroness, and he was at least more established than any other of her workers. Everyone else she knows end up living with her or at least closely working with her, so if she wanted to give the puppies away it would be to someone she isn't around all the time.
As for why Cruella would give him a dog, she indirectly caused him to lose his job, so she might have felt that this was a way to make up for it.
The Baroness introduces Roger to Cruella in one scene when Roger is established to be the Baroness's lawyer.
Why didn't the Baroness just put Cruella up for adoption?
It wouldn't be that hard for someone wealthy like her to arrange it. The two don't look terribly similar to each other, especially with Cruella's hair, and there weren't many people around since it was a homebirth. Just swear the servants to secrecy, give the baby to some other family or send her overseas, and never give her a second thought. Why immediately default to killing her?
The Baroness has such a big ego, simply writing Cruella out of the picture isn't enough. She needs to be absolutely confirmed her "obstacle" is removed completely. Just read her life's philosophy. Even a small chance of Cruella being around will make the Baroness "care". She also didn't want her wealth to be passed to someone else, on a plus note. So death is the best chance to stop that fear from coming true...
Does this film really set up Cruella as a villain?
The film portrays Estella/Cruella as being mischievous, willing to cheat and steal, but ultimately a good person who won't cross certain lines, and cares about dogs. Further, she realized that the Cruella persona was alienating to her family, and seemed to tone it down from then on. How does this set up the madwoman in the cartoon who steals puppies to skin for a fur coat? Or will this be addressed in the sequel?
Read Adaptational Backstory Change and Alternate Continuity. The writers are trying give her redeeming traits, and when it comes to a Complete Monster like her, it's bound to lose it's connection to the original character. How it will be be addressed, one can only wait and see. In short, she's not supposed to be 100% like the cartoon.
It does seem like the film is just trying to interpret Cruella as a lighter shade, to see how the character would work as a campy rebel icon who's seriously troubled, rather than a villain. It could also be read as Disney recognizing the appeal of camp but seeing the dark morals that are usually baked into iconic camp characters as unsuitable and unmarketable for a lead role.
Are Pongo and Perdita going to be parents and siblings?!
Not that unusual for purebred dogs. Or in the animal kingdom in general.
It pretty much to make sure all the puppies are full Dalmatians, and it does have a tad of Fridge Brilliance when you remove the incest part.
How does the Baroness not recognize her own daughter?
You would think the baby's hair would be a dead giveaway. A woman shows up years later with the same hair color.
How does inheriting Baroness' wealth work?
So, Estella is Baroness' dauther and heiress, fine. But she can only come into her legacy after her mother dies, right? And with Baroness arrested shouldn't the state seize or freeze her assets anyway? Also, unlike in "101 Dalmatians" where Cruella was an actual person, here it's just an alias, a stage persona. How could Estella legally will her possesions to "her good friend Cruella", when they're one and the same, and when Cruella has no ID or records to speak of?
The assets of the Hellman estate belonged to the late Baron, not the Baroness, which is why they're neither frozen or seized by the government.
Baroness not capturing Cruella sooner.
Cruella was not exactly subtle in her appearences. I would expect that after the first few cases police and/or Baroness' thugs would be lying in ambush at her next showing.
The Baroness would look very suspicious trying to intercept Cruella during a publicity stunt, and even if she succeeded in getting the attack out of the view of the public or achieved it with no traces to herself, Cruella would become a martyr. Following this, for the sake of PR, the Baroness would have to endure the humiliation of doing something to honor Cruella rather than forging ahead like she'd want and trying to pretend Cruella never happened. We see both of these happen in a smaller form when Cruella is attacked and assumed dead—she has a legion of fans willing to honor her at the Baroness' event and the Baroness is forced to pay tribute to her with a toast because a dead Cruella proved so beloved. The Baroness was undone by trying to eliminate Cruella by force. Her earlier strategy of trying to hold strong and outdo her challenger image-wise may not have worked, but it's possible she only would have needed to endure a few more Cruella sabotages before the public became sympathetic to her and saw Cruella as an unlikable aggressor. If anything, it wouldn't have absolutely ruined her the way the murder attempt did.
