Make no mistake, how many of this Isekai crossover series that Kadokawa can make, and Isekai Quartet will definitely not hesitate to slow down, with the endless list of Kadokawa characters this short can fill just to satiate us with the teasing of new characters, but with a cost of leaving them on the wayside. With Season 2 featuring the Shield Hero characters, and the aforementioned Season 3 (possibly) featuring the Cautious Hero characters (more or less), will this be a trend going forward, I totally have no idea, but just hoping they would've have just as enough screentime as the main cast.
I mean, if you've watched enough of Isekai Quartet, it's standard fare as with a touch of a button, the characters just come at the beck and call of the standard quartet gang of Overlord, Re:Zero, Saga of Tanya the Evil and Konosuba. Meanwhile the shenanigans range from content to content, but the real caveat has always been the huge cast of characters interacting with one another and the many classical noteworthy gags from the 4 series being parodied enough, so much that it feels fresh for other characters to "utilize" and make a joke out of it.
While Season 2 here has gotten better due to the chibi art refinements and how the production stuff find new ways to amass better content, this season really suffered on content that are hit and miss, depending on how the different characters react to real-world stuff and situations that are usual in their world, have different takes on it, spare the comedy that has good amounts of laughs. The music also took a hit, and if from a musical standpoint, it's still good, but IMO compared to Season 1, the OP/ED are good but unfortunately not as whimsical and lively as the former and depending on your taste for music, IMO lost brownie points here.
In a nutshell, Isekai Quartet as a series can be seen as the long-running short that will never stop as long as people have inputs and considerations of Kadokawa's characters being able to incorporate easily into chibi style and let them handle their shit alongside the formidable quartet, albeit still in that same school comedy setting. Still a good show if you'd ask me, but make the content a lil' bit more interesting when Season 3 rolls around, pretty please?