> Rather, it made me feel like an old fart using a computer for the first time, bewildered more often than not, most of my instincts rendered useless.

This captures the way I felt using Asana for the first time as well, about three years ago as a (not-that-old) college student. It was really hard to internalize its expected data model/flow. My team ended up settling on Trello. I've always figured that Asana was meant for larger teams and more complicated projects than I've been exposed to, but it certainly felt confusing as part of a small team.