We have driven a dozen times in Italy.. always in an intermediate size car (mostly due to a need for a 4 to 5 passenger car)
This trip...for almost 2 months.. there are just 2 of us. Choice 1 (with Europcar thru AutoEurope) is about $1800 for a mini/economy car. Choice 2 $2300 for a compact car...both choices are 4 door.
In talking to AutoEurope...they suggest the economy choice..saying that in many cases at the time of pickup it turns out there are no economy cars so the customer ends up with a compact anyway...thus saving $500 (although obviously no guarantee)
The last rental we had some nice amenites..an IPod dock , fold away mirrors etc. (priceless in Sicily)
Anyone have a firsthand experience to help us decide?
It has been difficult to get an explanation that makes sense..both cars seem almost identical. But $500 is a bit of money..not to be spent without good cause
Our trip ranges from Ortigia in Sicily (very narrow streets for a big car) to the hills in Umbria

We generally get an economy car primarily to make it easier to navigate the narrow roads in many of the towns and villages. It doesn't have all the amenities u describe, but works fine getting us where we want to go and ok comfort wise. U would likely save on gas too. We travel lightly so the small trunk size hasn't ever been a problem 4 us. I don't even know how many rentals we've done in Europe and we've never been offered a free upgrade to a larger car, so I wouldn't count on that (and we do rent either thru Kemwell or Auto Europe)
Have u looked into a lease program? Never done it, but supposed to be a good deal for that long of a time period.

Do you plan to do much driving on the autostrada or mountains? If not, the economy will do. Its smaller size will help navigate streets and I have found the newer models to be comfortable. They may be strained on the autostrada if you really want to make time, but on the other hand will cost less at the tolls if I recall correctly. Cars that I have rented in Italy over the years include the Fiat Panda, very small and probably too underpowered, but it did get us through the Dolomites with a lot of gear rowing, the Fiat Punto and Fiat Uno, nice cars that did all that we wanted them to do and were easy to drive (we have rented several of these), a Fiat Uno in Sicily, the Fiat Steelo (sp?) that was a size upgrade and was very comfortable and good on the autostrada, and a Smart 4/4 that I drove on the Amalfi coast road with 2 friends crammed into the back seat, also with a lot of gear rowing but it was quite a nice car to drive.

yestravel
Thank you for commenting on the no economy to compact upgrade...Whenever I get a suggestion from a company rep.....

Have you checked out the lease buy back program from Kemwel?
You can do it from Rome.