It seems like I'll be one to go against the flow here. I liked this one. I never really minded the modern dynamic of Skinner & Chalmers so to get an entire episode focused on them was an interesting prospect & having it be a road trip story about the odd couple ending up going to Cincinnati together by car to an educational conference Chalmers will be attending was a simple but good premise. In the end, I'd say it worked out fairly well and presented itself as an entertaining, enjoyable episode with a bunch of nice and fun scenarios and jokes (all being typical to road trip stories), no intrusive subplots, pretty decent pacing and good animation. It was probably not one of the all time best modern episodes and was at times really silly, but I thought it was decent and I had a good time watching it. After a very forgettable and lackluster previous episode and a few other disappointments this season it stood out as one of the better outings so far.
It got off to a decent start with Chalmers holding the principal meeting where he announces the plan to go to the Cincinnati conference with a principal, although I do think Skinner was a bit too pathetic (making an forced "joke" to be noticed and failing to do a simple high five, ending up slapping Chalmers' crotch instead, even if the reaction did make me chuckle). Also, I did not care for Principal Finch whom is so liked to the point of being Chalmers first and obvious choice (weird how he was portrayed as supposedly funny and cool to the others sans Skinner, but I just found him pretty obnoxious), but he was more like a plot device than anything. I did like the detention scene with Bart giving Skinner advice to stand up for himself and crash Chalmers' trip (and Bart's line about Skinner "spending his life with his hand stuck in a pelvis" made me chuckle despite being lame). So Finch is being held up by having eaten bad fish or something the night before and Skinner happens to show up infront of Chalmers in a taxi to take Finch's place (I already suspected foul play here, but as I didn't like Finch I didn't really care).
The airplane scene with Chalmers having a bad case of aerophobia (fear of flying) ended up pretty amusing with him freaking out all over the place with his delusional ranting (the emotional support animal gag with the plane packed with people having various animals was amusing plus I liked the lame joke about 'Game Night' & Jason Bateman appearing speaking to Chalmers through the movie). So both are kicked out and Skinner goes to his mother Agnes and gets to borrow her car so they can drive instead in an kinda nice little scene (and I liked how it wasn't too extreme). Then the titular trip gets going and there's some nice back and forth between Skinner & Chalmers, I enjoyed the joke with the trio of young improvisational Shakespeare actors & the crash into a silo of giant soy beans (which has the car eventually randomly exploding) was an amusing turn. Then there was the Conklin bit with Skinner weaseling him and Chalmers out of court by helping out the female judge (who reminds him of his mother, whose sheriff son is a Skinner-lookalike) which grants him a loan of her car so they can continue their trip & it was entertaining for what it was.
I enjoyed the biker bar (which turns out to be a professional cyclist bar, which was a pretty good subversion) joke scene with the cyclist stereotypes (bike computers, sipping hoses & whatever) & how Chalmers was the one messing up by angering the cyclists yet again, as he was the one who crashed the first car (As usually it is Skinner who gets them into trouble. Having Chalmers be fallible does improve the character with a bit of development). There's a ridiculous chase with the cyclists pursuing the duo's car (in true Scully-like fashion) & Skinner bringing in the wheelchair-bound war veterans with ripped arms who scares off the cyclists was an equally ridiculous bit, though I still thought is was decently fun. The bed & breakfast scene was a good one, with the drama between superintendent & principal when it turns out Chalmers was going to fire Skinner and replace him with Finch & Skinner turning out no better (being responsible for having made Finch temporarily sick with black mold, which was awful of him); I enjoyed their fight scene (felt like this was the culmination of their pent-up enmity through the years).
Then the last part begins and it was a good one. So they accidentally swap jackets as they part ways as foes (which I saw coming, as I thought there was something visually wrong with the coats the other one was wearing) & it turns out Chalmers doesn't have his speech note but only Skinner's lame opening jokes, which sees him improvising a speech on Skinner (which goes from shaming the principal and being a hypocrite, as Chalmers too did cause problems on the road, to realizing that he actually likes and respects Skinner due). This was a solid end, even if Chalmers change of heart happened a bit quickly in the end, plus it had a nice finale with Skinner rushing in with the superintendent's speech and hearing the praise (their reconciliation did feel pretty rewarding). Sappy but it worked. Chalmers holds his speech and everything goes well (at first I thought there was gonna be a joke about the speech being boring or something, but it never happened) and Skinner feels good about getting what he wanted (Chalmers now liking him) and tells Bart about it in a nice wrap-up scene (followed by a brief bit with of him & Chalmers at a café).
As for the Simpsons, their very minimal role here felt unusual. Only Bart had something of a role in the episode (and Lisa appearing the jump rope skipping gag at the beginning and the end) and Homer & Marge were nowhere to be seen so I wondered if they weren't gonna get any lines (I knew they were bound to at least appear once, having seen that promo image with them on it). Then that last act scene comes with the dinner scene and in which has Marge speaking a bit and Homer gets line. The scene itself felt kinda forced at first with Marge asking how their day were (when we didn't get to see it) and more like filler, but then Marge reveals they are going to watch the Shakespeare improv trio perform, nicely tying in with the rest of the episode with a funny little end scene of Marge loving the performance while the other Simpsons are just bored. That was a nice final bit even if it was unnecessary (and unlike most times, it didn't take away time from the rest of the episode, which skipped the intro as most Selman episodes do and got to the story right away, which is always a good sign).
So all in all, I very much enjoyed this episode as said. It had a basic premise with Skinner & Chalmers on a misadventure-filled road trip and managed to deliver a nicely paced and entertaining story with a bunch of good scenes and nice little jokes and gags (more or less silly) and some good drama & a sprinkle of emotional content (I was surprised they actually took the Skinner-Chalmers relationship decently seriously without making it a farce, despite all the silliness. The bed & breakfast scene was one of those scene that helped cement the serious side of their conflict). The road trip story worked well with the duo and it gave some nice development to both by making it fairly character-based (in a sense, this episode was sort of their version of what 'King Leer' meant for HD era Moe). I wouldn't say it was a great episode, but it still had my interest despite not having any big surprises or super memorable setpieces. It could have been better, but I still liked it.
Going to give this 4/5 for the time being. Maybe I was in a good mood (and I didn't have any especially high hopes) but as for now, I found it an entertaining piece. Not a fan of Jeff Westbrook (one of my least fav modern writers) but this is probably one of his best (and Selman should get credit for pulling off the showrunning aspect).