Earlier quoted context omitted.
If it's your first time in a new city, you probably just want to get to your hotel as fast as possible instead of learning the transit system.
I've only traveled in Europe and Asia so far but this never looked like an issue to me. Also I'd also use the transit system for the following days in the city, so have to learn about it anyways. (Not that there's really anything to learn)
It’s not pleasant in cities with great transit like Tokyo or Seoul, and it’s downright miserable in most of the cities being discussed here in this thread.