Well, you sure found the right place on these boards because you can search a topic or just ask a question and someone will help you.
We did the land/sea two years ago. It was our first cruise experience. We planned everything ourselves and it really is not that difficult.
I booked the land/sea through
DCL. The category on the ship will determine where you stay. Not all resorts are available to choose from. There are no value resorts. We were in cat. 11 (loved it by the way) and we got to choose between the POR and CR at the time. Of course, the higher the cat., the higher valued resort you get to pick from. You can easily get a quote from the disney site.
We used the buses for all of our transportation needs on that trip because it was easier overall. Now, I book my own towncar (we use Tiffany Towncar). at the top of the board, there is a section on transportation. The main reasons are the crowds, waiting for buses to fill up and not being able to be picked up at the resort until 11:00 at the earliest I believe. We were at POR and the bus comes around 12:15 and now they are letting passengers on the ship around 11:45. We didn't get there until well after 1. With a shorter cruise, the time really makes a big difference to me. Plus, if you want spa or Palo (adult dining) reservations you will want to be there early.
If you want to add on days before or after your trip (beyond the land/sea) you will have to make those reservations separately.
Don't use DCL airlines. It way to expensive and sometimes the times are not very good.
Those are just some basics. Ask away and have a great time!