Tabi Machi Late Show was a collection of 4 stories, each one taking up a single 7-minute-long episode. This meant that it didn’t really have time to develop, or even properly introduce, any of the characters, nor were the stories very complex. The animation was also very minimal, but I think the show’s visuals served their purpose more than well enough.
As the synopsis on MAL says, the show is about goodbyes and/or journeys. In fact, all of the episodes except the secondnd one are about goodbyes and journeys. The first and the fourth episodes are pretty simple and down-to-earth, while the third one is almost fantasy-like (but by no means worse than the first and fourth episodes, at least in my opinion).
My favourite episode is the second one, though. Rather than being about goodbyes, it’s about realising who you want to say “hello” to, and in that I think it’s a greatly uplifting story, even if it has a bittersweet overtone to it (like the other episodes). I was able to relate to the characters in that particular story (even though they had barely any introduction), and I felt like I learned something from it as well. Good show.