You need to store the start of the time period somewhere. A very good place for that is NSUserDefaults
(tons of tutorials out there on how to store and retrieve data).
Then you need to read that data and calculate the difference in days / weeks (basically 7 days) / months between the stored date and the current date: Days / Weeks1 - Days / Weeks2 - Months
The next step is to actually rotate the image views. That can be achieved by setting the transform
property (be aware of radians vs degree):
imageView.transform = CGAffineTransformMakeRotation(numberOfDays * M_PI / 2)
If you try all that together and encounter a serious problem that has not been asked and answered on SO already, feel free to ask another question.