It is very overwhelming it first. I think if you do it in stages, and break it down, it gets easier.
The very first thing you need to do is either get a big piece of paper and draw up a crude chart that has your "days/dates" listed out. If you're computer savvy, just draft up something. Then pick your park days. You can do this any way you want--you can just pick or you can use one of the crowd predictor websites.
After your days are picked--decide if you want to do any sort of special dining experiences. These would be things like the Hoop Dee Doo Review, the Luau at the Poly, a Fantasic dinner package--something along those lines. These types of things will take longer than the average meal and you might want to plan these on certain days. For instance, if I do Hoop Dee Doo, I will ALWAYS do that on a Magic Kingdom day because this dinner show is easiest to get to by boat from the Magic Kingdom and I always do the early show. So my Hoop Dee Doo will always be penciled in with my Magic Kingdom day. Or if you decide you'd like to do the Liberty Tree Tavern, you'd want to do that on your MK day also.
Then decide if you want to do any signature dining. These would be places like Citricos, Cali Grill, Narcoosees. Figure out which one you'd like and see which park day it would fit in best with. Do you want to shower and get dressed before you go to one of these? Then you might opt for penciling this in on a day where you know your park day will be short (Animal Kingdom?).
You really need to build your park itinerary first. I find my plans fall into place after that.
Since you are unfamiliar with the restaurants, it's great to take some time to read the dining reviews on the dining review board, although, I went back to that board this year prior to my trip and it had changed. Lots of PRE-dining review trip reports, lots of posts that seemed irrelevent to the reviews themselves. I found it difficult to wade through. But see where other people are eating, try to get a general sense of a place and look for ones that seem to consistently get great reviews. Every place will have a bad review here and there but you don't want them to dominate the overall comments.
Think about your needs/likes as a family when you view menus at allears. I also buy the Unofficial Guide because sometimes I like things more summarized and I get tired of staring at a screen.