Michael,
As you're going to be covering a number of different areas in the country, the Italy 2014 book would probably be the best choice as it covers all the areas you'll be visiting. AFAIK, it has more information than the "Pocket" books but not as much detail as the "City" books. However in my experience, the amount of detail provided in the larger Guidebook is MORE than adequate.
The Planning Map is somewhat "basic" and doesn't show much detail. I'm not sure which map comes with the book, but all of the Maps are available separately.
On the topic of luggage, I'll preface my comments with the disclaimer that I don't use Wheelie Bags. I prefer a properly fitted Backpack. If I was going to buy one of the RS bags, the Rolling Carry-On would be my choice. The combined Rolling Bags/Backpacks have some "issues" which make them less desirable. For example:
- The extra weight of the wheels and handle mechanism will add to the weight being carried.
- Some people have reported that the wheels or frame "dig into" their back, making them uncomfortable to use as a Backpack.
- That type of bag usually doesn't have a waist belt, nor does it provide any means for torso length adjustment. That means ALL of the weight will be carried on the shoulders instead of being partially being carried by the hips as it should be. There certainly could be some bags of that type that address the problems I've mentioned, but I haven't seen one yet.
To summarize, the combined Rolling Bag/Backpack is a GOOFY IDEA (IMO) and I'm surprised that RS is marketing something like that.
Good luck with your choice!