Continuing the discussion from "Betrunkene" near Mallorca:
As OpenStreetMap is apparently really important for Apple maps now, at least in some regions, maybe we (the OpenStreetMap-Foundation) could try to ask them again if they would be willing to give us (the mappers) the right to extract information from their street view imagery for inclusion in OpenStreetMap.
Slight disagree because Apple Maps still doesn’t say how old street imagery is, so someone might be unintentionally using 5-year-old imagery in which none of the stores shown exist anymore
I’ve just checked and had no problems finding street image date on my iPhone, I only need to open the image in full screen and then go to settings and details.
This browser also shows image timestamp:
https://lookmap.eu.pythonanywhere.com/#c=15/39.376588/21.599788&p=39.376588/21.599788&a=0.00/0.00
there is much more than shops that can be derived from street imagery. Also for aerial imagery we do not always know / it is not always stated from when they are, but still they are typically considered useful.
I agree that every data source has their specific limitations and it is good to be aware of them.
That’s not a unique problem. Other imageries are still used without knowing the exact date. It’s the user’s responsibility to judge whether it should be used.
$5 million $ / € / £ a year as thanks for providing their base-map! 
Also has extremely limited coverage. Just London and Edinburgh in the UK is all I can find.
The overview nicely shows which countries Apple Look Around has focused on so far:
https://lookmap.eu.pythonanywhere.com/#c=4/51.108286/2.976433
Just had a look in my area and would say the coverage is better than Google street around here. Could be a great help here and there as an additional source.