The choice of the Jungle Book characters who made it into the cast, compared to the others. Baloo already works on this hind legs like a human in the original movie, so he'd fit easier in an anthropomorphic society. Louie's whole deal in the movie is that he wants to be human. And Shere Khan comments about how business is like a jungle himself in the pilot.
This also explains why the Talespin version of Louie is depicted as, oddly, having a more ape-like pose than he did in the movie, whereas all the other Jungle Book characters underwent an Anthropomorphic Shift. He's not trying to be a human anymore.
This is also the reason why Hathi and Kaa were not included in the series: an elephant, and especially a snake, is more difficult to anthropomorphize compared to a bear, ape or tiger (that said, elephants occasionally appear as background characters, and one Villain of the Week, Thaddeus E. Klang, is a snake).
Mixed with Fridge Horror. At the end of "Her Chance To Dream" you're probably left wondering why Rebeccca didn't just go with Captain Stansbury and take Molly with her. Well, Stansbury is dead. That implies that Rebecca would have to die in order to go with him, and in order for Molly to go with them, she'd have to die too.
"For Whom the Bell Klangs". The two-parter's main antagonist is Thaddeus E. Klang, a villain who seeks to use the bells of Tinabula for his own ends. He kidnaps Katie Dodd, who has the Three Bells of Tinabula in her possession and can interpret Tinabulan hieroglyphs. Tinabula is a city that works on sound. Thaddeus E. Klang is a snakenote Snakes, such as cobras and vipers, were widely believed to be deaf., so it's natural he would seek help of a fox, who has some of the best hearing in the world.
Baloo and his friends live in a fictional counterpart of the United States called "Usland" (never stated in-series, but according to Word of God); in their universe, the fictional version of the Soviet Union is Thembria (stated in-series). When taken together, the names can be taken as puns (us = the USA/Usland; them = the USSR/Thembria).
While Rebecca does run a tight ship on Baloo, she sometimes can be just as strict toward Kit (though Kit seems able to bear it more easily than Baloo). But consider this, when Rebecca first met Baloo, he already took Kit in as his navigator and a de-facto adopted son, and the way Baloo acted towards her as well as how messy his office looked when she first arrived likely gave her the first impression that Baloo wasn't the best of role models, So Rebecca likely felt she should try to make Baloo a more responsible and disciplined employee so he'd be a better influence on Kit.
In the opening movie, Baloo asks Kit to explain how he got mixed up with the pirates. Kit says that he joined up with them about a year prior to the story's events but got "sick of it". Now that begs the question: "Sick of what?" Though given that Don Carnage was willing to throw Kit off the Iron Vulture, we can probably guess.
Added to this is that while it's not outright stated, it's pretty much canon that Kit is an orphan. So it's entirely possible that Carnage lured him aboard his ship with pretty falsehoods and by the time Kit realized what he had gotten into, he had nowhere to go.
Several episodes imply that Rebecca actually had a Friendless Background, her attempts to mingle with high society usually fail because she is actually poor, while, being the thirties, she sometimes earns scorn as an entrepreneur due to being a woman. Generally her only close friendships shown onscreen tend to be among Baloo's team. This also adds Fridge Brilliance to Becky's Tsundere attitude and frustration whenever Baloo doesn't seem to appreciate her, not to mention why she insists on dragging him along in almost everything.
"Bygones" features an aged World War I combat pilot who called the Sea Duck "newfangled". Baloo responds with "The Sea Duck's 30 years old!" The show takes place in the 1930s. Something doesn't add up there...
It slowly becomes clear that the 1930s aesthetic of the show doesn't mean it's our 1930s. Not much sign of Earthlike geography, or wildlife: one episode features the first experimental jet turbine in Cape Suzette (making it around 1944-1947 by our history), but we can't expect the show to stick closely to the history of airplane tech when higher priorities like the Rule of Cool and Rule of Funny are at stake.
A date on a newspaper and a comment on the Yankees, both found in the "Plunder and Lightning" pilot episode, would place the show in an alternate history 1941. Concerning the Sea Duck's age, Baloo may have been rounding up by a few years. To handwave it, you could actually just blame it all on Wildcat, the mechanic. Judging by his skill in and odd manner of fixing things, it isn't too hard to believe that there is not a single inch of the Sea Duck that was part of the original plane.
Not to mention in the episode "Your Baloo's In The Mail" where Rebecca says her mail with her contest winning ticket wasn't important because she fears Baloo won't take her request seriously, but is insistent that Baloo must use the fastest mail service around. If Rebecca had been honest with what her mail was, or if Baloo had just listened to her and realized that if someone is so insistent about using the best postal service method around then their mail must be important regardless of what else they tell you, a lot of trouble would been avoided, meaning they had two different ways to resolve the problem and in the end failed to do either which led to the Downer Ending that upset so many fans.
"A Baloo Switcheroo", the episode with the soul switchingidol: They cooked up a zany scheme to seed clouds, even created a hurricane by accident, in an effort to create lightning, when clearly, just a few seconds before, we are shown that the idol's power could be triggered by a mere wall socket, which is how Rebecca and Karnage are switched. Karnage's tail gets stuck in a wall socket while they both held the idol and were looking at it, yet nobody seems to notice this fact.