It is complex enough (sound engine, GUI design, library manager, metadata editor, SQL database design, SQL database management, SQL queries, playlist management, playlist editor etc. etc. etc.) that one person easily can loose oversight. If not planned/designed/programmed/tested properly this many problems can happen. Probably a very small team worked on AS also.
I have the impression, like others already mentioned on this forum, that AS is rushed to quickly, thereby missing some steps in the implementation chain. Also as a small company (mostly one man) Audirvana lacks the experience to implement a trajectory like this? Therefore the planning was too optimistic but dates where already set? (The remote app still is not available, a miscalculation again?). Who knows.
But to build the application, with all the complexity that you detail, was not started from nothing. A3.5 served probably as a foundation for all the main features of AS. Because except the radios and podcasts, and some side features like the MusicBrainz tag, As is offering much the same as A3.5 in a new look.
And for the planning, Damien could have foreseen that it is rushed. You don’t have to be a computing engineer to realize, for instance, that the player lacks a remote.
You or I can only fully understand it if we where there . I was not, you where not, so it is just guessing.
I know from my own working experience, as a developer in several teams, on larger projects that it is never as simple as it looks. Even with an experienced team and project management, unexpected problems and setbacks occur.
The industry in which I work is in the field of arts, and creativity is not something that is easy to plan. The projects that are developed and produced can be very complex, and can evolve hundreds of people if the project is big. The budget of a single project can reach tens of millions of euros.
Eventual setbacks are always a part of the planning and are budged ahead, because we expect setbacks to occur. But there are working methods in order to guarantee the release of the finished product at the date that is scheduled ahead.
EDIT
And unlike software, the products can not be improved with future versions. Once they are released, nothing can be changed. They have to be good at their release, because there’s no second chance to improve anything.
. I was not, you where not, so it is just guessing.