Look at other companies that does map, google map started out using Tele Atlas, NavTeq serves yahoo, bing and mapquest. Let's face it, spatial data cost money to collect and even more costly to update/maintain. Nevteq and Tele Atlas are gigantic companies for serving basic spatial data for a reason.
I guess apple didn't do sufficient data QA before saying, "hell yeah we are going with OSM where every big player is going with commercial data."
Without a solid baseline data, any fancy pants software development would just evaporate in air.
I have to say though, the GUI for apple map and functionality has very high usability. Apple just need to adapt a different mindset when dealing with data-dependent applications.
(disclaimer: I am a PhD student in Geography with CS background, did my share of processing spatial data for the last 8 years)