Hey Date twin!! I would start now. If you are using the resort photog with the free package, you would want to make yourself known to him. If you are going with one of the other packages, I think your time will be blocked. If you need more time though, you would want to tell him.
I am using an outside photog and I had to book him 3-4 months ago.
I also used silk flowers, so I booked that in November.
My TA has the contact info for cakes/flowers, so I just have to send her pics and she takes care of the rest.