I really dig your question because my wife and I went on a number of Disney vacations together before we had our children. So, I'll start with your second question and then pull a slick segue back to your first question!
As far as your itinerary goes, I'd suggest letting your dining reservations drive your plans. I've found that if you pick some great places to eat, your itinerary will easily fall into place from there.
So, that leads me back to your question about table-service dinners. As you've probably already discovered, there's a wide spectrum of dining experiences to choose from at Walt Disney World. As I see it, you compartmentalize the table-service restaurants into the following types of dining experiences:
3) Novelty/Whimsical; or
4) Stick-To-Your-Ribs Good Eats.
When my wife and I were in your shoes, we tended to gravitate more toward the "romantic" and "good eats" experiences.
So, if you're looking for a romantic dinner, you can't go wrong with places like: The California Grill, Le Cellier, Jiko - The Cooking Place, Artist Point, or The Hollywood Brown Derby.
If you're looking for some "good eats," you can't go wrong with places like: Chefs de France, 'Ohana, Liberty Tree Tavern, Via Napoli, or the 50's Prime Time Cafe.
Here's a little tip from your buddy Derek:
If you are having trouble snagging reservations, don't give up. Cancellations happen all the time, especially within a few days of a particular date. Also, walk-ups are possible in some instances, but you have to be there right when the restaurant opens for service.
I hope that helps! If you'd like the inside scoop on specific restaurants, please feel free to write back and I'll be happy to share my thoughts.