I know the mapkit does not support street view but it is possible to render it in a web control (as shown in another stackoverflow post: Google Map Street view in Iphone app).
However, in the Trip Adviser app, they have mashed it up with a A.R control. Again, I can probably do the AR bit but how do I get the angle from street view. E.g, what the user is facing?
TripAdvisor have answered your question: http://tech.tripadvisor.com/2011/02/augmented-reality-on-ipad-project.html.
Pin Positioning is described in the blog post.