You must be in a motel and have slept in order to make a new checkpoint.
Then you can proceed to knock on all the motel doors for the money drop, and after you got it you can safely click restart on the pause menu and repeat the process all over.

Take into account that knocking on the doors will probably get your trunk searched in the checkpoint, so if you want to avoid this you should restart once more and avoid knocking on others guests doors.
It is recommended to do this in the turkey motel since the night is the most expensive (45 marks).