Bob:
Many travelers will say you've scheduled simply too many stops in too many places. Cities are often somewhat like cathedrals and churches--they all get to looking alike. I'd like to see some of your cities, but there are just too many great hill towns and popular places you've left out.
Like many travelers, $9.50 per gallon gasoline has slowed us down greatly, and we really like staying 4-5 nights in one area--doing day trips to surrounding towns. We get to know the area better. We'll then move on down the road to another area/region of interest.
When we were in Tuscany and Rome Easter before last, we had no problems finding accommodations @ 70 Euros per night. Virtually every farm in Tuscany has apartments and rooms for secondary income, and there are hundreds and hundreds of agriturismos available. We spent a long weekend in Florence, moved out to Chianti to an agriturismo, did a day trip to Venice and spent the balance of our trip in a B&B outside Rome.
We now research rooms carefully online, even going as far as looking at TripAdvisor.com and RickSteves.com for customer recommendations. I've also used Booking.com filtering by the cheapest price and then looking down the list for those places with extremely high customer recommendations. I've never been dissatisfied with any accommodations thru them.
AirBnB.com is another upwardly moving website for budget accommodations.
Remember that there's no way you can see everything on one trip. Why don't you pick 3-4 cities you really want to see, and limit your stays to close by those cities?