These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Alternate Character Interpretation: Are the Ross parents extremely successful celebrities who are simply too busy maintaining their financial empire so that their children can afford keeping Bertram, Jessie and all of their material possessions around and legitimately love their children, or are they irresponsible self-absorbed attention freaks who have clearly adopted far too many children just for the sake of appearances and have left them to be raised by money, resulting in four clearly spoiled brats?
Is Jessie really a Magical Nanny or dangerously incompetent and ill-suited for the job? Even the show itself has a hard time deciding.
Also, Jessie is engaging in Obfuscating Stupidity. She can fly a helicopter and was a straight-A student in high school, after all.
The same can be said about Ravi. His "relationship" with Mrs. Kipling is pretty annoying as is the way he treated her young. At least Zuri and Ravi both have some of the funniest scenes, but at the cost of simultaneously being two of the most annoying characters on the Disney Channel.
Ear Worm: Even if you don't like the theme song, you've got to admit it's catchy.
Ensemble Darkhorse: One of the most popular characters in the whole show so far is Creepy Connie - a character who not only was meant to be as close to walking Nightmare Fuel as a series of this nature would allow, but also a character who has appeared in a whopping two episodes.
Officer Petey, who has now appeared in two episodes each season so far and certainly in future ones.
Arguably Nanny Agatha, who's appeared in as many episodes as Officer Petey has so far (including one with Officer Petey)
Fridge Logic: Jessie states in "Tempest in a Teacup" that her prom ended with her embarrassment at her Senior Prom. Prom is typically in May and she graduated in June. She arrives in New York in what appears to mid to late summer or early fall. She either left very soon after graduating and didn't get to New York City months later, or had many more of her wrecked relationships after graduating but before packing up and leaving for New York. Either way, while she didn't have the best life in Fort Hood, Tx, the Prom incident is more than likely what caused her to leave town. Going to New York is just a side bonus. And why didn't she choose Los Angeles. Make you wonder about her, not to mention What Might Have Been had Jessie gone west.
Fridge Horror: In "World Wide Web of Lies," Mrs. Ross tells Jessie that she's under 24 hour surveillance, to the point where they know of Jessie's sleep-eating (which Jessie herself doesn't even know).
"Funny Aneurysm" Moment: After "The Whining" aired, a nanny in New York did kill two of her kids like the Ross children thought Jessie wanted to do. Disney has since pulled all reruns of the episode and it was removed from iTunes.
The pulling of the "Quitting Cold Koala" episode can be considered this as it was pulled before being aired due to jokes made about Gluten-free dieters. It was to air in May of 2013 and May is National Celiac Disease Awareness Month. People with Celiac Disease cannot eat gluten.
In-universe example: In "Gotcha Day" Bertram warns Mr. Kipling that if he ever has kids Bertram will make omelets out of them. In "The Secret Life of Mr. Kipling" (which happened to be the very next episode,) Mr(s). Kipling's unhatched kids are in danger by being trapped inside a restaurant - that specializes in making omelets!
Girl Show Ghetto: Averted by using an equal cast of three guys and three girls, giving both the male and female characters important (if not entirely equal) roles and attracting both male and female viewers with eye candy. You can take the viewpoint that the show is slightly shifted more towards girls because Jessie herself is the title character, Peyton R. List is the second actor billed & Zuri is the first regular character the audience is introduced to after Jessie.
The plot point of the episode guest starring NBA All-Star Chris Bosh, who plays for the Miami Heat, has Luke trying to and seemingly suceeding at washing Chris's lucky socks, rendering them useless and causing Bosh to lose all of his skills, so the Knicks can beat the Heat. Considering that television episodes are typically shot at least 2-3 months before their air date, the episode was more than likely shot before the 2012-13 NBA season had started. New York and Miami have played each other twice between filming and the air date, and the Knicks won both games.
Add to that Lebron not scoring 20 or more points in a game for the first time all season right around the time of the promo started running and that the Knicks got off to one of their hottest starts to the season in franchise history makes its even funnier.
Hollywood Homely: Jessie, played by Debby Ryan, is occasionally made fun of for apparent physical imperfections. Though that might be the joke.
Incest Yay Shipping: Suffice it to say that every one of the Ross children has been shipped with another one of them.
From the same episode, losing track of a child under your supervision must be unbearable when you consider what happens to most missing kids. Zuri even says to Jessie when they find Emma and Ravi, something along the lines of "I told you they would still be alive"
Replacement Scrappy Series: Some people had this attitude when Jessie first premiered regarding Suite Life on Deck. Note that people also thought the same when On Deck replaced Suite Life of Zack and Cody.