>to the point that it makes me completely lose trust that any thought has been put into the human factors of the rest of the system.

This doesn't really make any sense. The issues with the file chooser are known, what's missing are design and development resources to do a redesign. The main problem is actually that the human design effort is being put into the rest of the system and not here; losing trust because of this is somewhat of a self-sabotage that you probably want to avoid.