It's been about three months since I started researching and planning our grand voyage. I'm going to try and give you some tips and advice based on what I've learned.
Here's the first big tip. Google Earth. I can't tell you how valuable this tool has been in researching places to stay, sites to visit, the best viewpoints for vistas, the best scenic drives, where to park, and how to avoid the dreaded no drive zones found in most tourist towns (zona traffico limitato).
Google Earth is easy and free to install. While Google map is best for planning driving routes, Earth allows you to save pin maps sorted by folder for each region or town you will be visiting. I have a folder for Puglia a folder for Rome and so on. I've pinned the best parking spaces, best views, hotels, bakeries, delis (salumerias), cheese shops, Hertz locations, and of course, all the sites I'd love to see in a given area.
And the best thing about Google earth is dragging the little man to see the street level view, in 360°! This can prevent you from booking and agriturismo that looks more like a factory, how seedy a particular neighborhood really is, or how thick the crowds really are at all popular tourist site so you can plan accordingly. You might even discover areas worth visiting you had no idea about before actually seeing them on Earth.
Try exploring with Google Earth months before your trip. It's both addictive and enlightening. My son doesn't want to see too much on Google Earth because he wants to be surprised... But after all, I'm the grown up and realize that surprises while traveling is not necessarily a good thing.