There is never a good time? or there is always a good time? are you afraid your hair is not ok this time or your son has a bump on his forehead or your baby is teething? there is always something, right? do not fret my friend with the right photographer magic always happens. This mean spending good amount of hours on editing and massive amount of experience but it is doable. what work always in my opinion is to bring everyone outdoors to feel free and let them do what they want in their own time. additionally as an experienced family portrait photographer I can say; the time is now! the only thing that matters is to have that moment in time captured, framed and displayed for everyone to see and to make them happy.