UPDATED: Car Rental Questions (companies, drop off fees, etc)

Agree with all of the above. Are you SURE that paying a $500 off fee is really "your best option"? Most of us would probably be able to find a better option (also check to be sure that the off fee is "just" US$500 - that actually sounds a little low to me). (note: the website seems to not want to allow me to type the word "d-r-o-p-o-f-f" for some reason) You are not going to know exactly what kind of car you will end up with, so let go of that. Be prepared to be somewhat flexible. Be very careful about expecting a credit card to really provide full CDW, and even if it does, be prepared for a major hassle in case you need to use it. After having a tiny bit of body damage once on a rental when I had used my "gold card" for CDW, I learned that it was not worth the time and expense that resulted. This was from a small dent in a fender that occurred while the car was parked, and this was a domestic rental (Hawaii) from one of the big name rental companies - it turned out to be an expensive, months-long headache that I will not repeat - now I always just pay for the zero-deductable "super CDW" that the rental agency (usually) offers. Yes, it costs a few bucks more, but it offers peace of mind. Don't reserve two cars unless you'e prepared to pay for both. I've had great experiences booking rental cars through gemut.com (they focus primarily on Germany/Austria, but I believe they also do rentals for other countries too). Their website has a wealth of info about car rentals - highly recommended if only for a free education.

In Europe I would probably go with Europcar or Auto Europe. Any driving in Italy will increase your car rental expense mainly because you will have to purchase more insurance than in some other countries. Drop-off fees in a different country are very expensive in Europe, probably especially if you are dropping off in Italy. I doubt that you will find a credit card that will cover all your car insurance needs for driving in Italy.
You will need to check the GPS to find out which ones come with European maps. Tom-Tom has at least one model that comes with Euro. maps already loaded. Don't know about the others.

1. I use local companies if the deal is better (Ireland, mainly). 2. There are no HIDDEN fees.... everything is spelled out in the rental agreement, but you have to read it and ask questions of the company. 3. Permission for what? If the company knows you are taking the car to Italy, then what other permission could you need and from who? 4. I have rented Opels several times with no problem. As for "bait and switch", no company will guarantee you will get exactly the car you reserved (even in the US). You could reserve an automatic and find none available when you arrive, etc. 5. Yes, buy a GPS before you go, so that you know how it works and won't have to fumble with it AND the rental car. 6. Credit card insurance won't cover you in Italy.
7. No idea, never done it. But if you decide to double book make sure you understand their cancellation policies. You don't want to pay fees to the other company if you don't show up for their reservation - and how will you know there will be a problem until the last minute?

I'm pretty much aligned with Nancy except for a couple of caveats: 1 - You can rent the car in another country, drive it in Italy, and take it back to the original country (or a third one) and still be covered by the credit card insurance. I do that all the time - - I try not to rent in Italy due to the cost. The governing fact is where the rental transaction actually takes place. You've raised an interesting point, since the tail end of the transaction will take place in Italy. You need to nail that one down in blood with the rental outfit - - my suspicion is that you'll need to choke the cdw the whole period out of your own pocket, but that's only one idiot's guess - - if I had the least trepidation that I wouldn't be covered, I'd buy the whole cdw - - you tail's hanging out in the breeze if you don't. 2. You're probably not going to find anything but a major company that will let you pick up in one country and drop in another. 3. You probably aren't going to get that Opel, only something in that class - - read the fine print. Also, even if you get the Opel, it might not have a hidden trunk since those gizmos that cover the luggage area tend to get lost/destroyed somewhere along the way. 4. Don't double reserve. If you don't get what you want/reserved at one outfit, take your reservation over to the next outfit's corner and ask them to match it. They will, everybody wants business. Final thought, do with it what you will: You can leave Rome early in the morning and drive to Nice for lunch. Nice has an airport. Juggle your sequence and it's less than three hours to Nice from the CT.

Be very nice to the car rental agent and ask how their day is. As you start the process, ask what kind of car he has for the category you are in, and why ( "I have 2 teenagers" or whatever). Let them know you want a car with a trunk and 4 doors. I've been upgraded by car people almost every time. Some renters don't care what kind of car they have; it is up to you to let them know in the most respectful and courteous way possible that you'd really like a 4 door car with a trunk. And say thank you! The insurance is going to be quite costly- have you actually plugged in the days and off locations in some of the search engines. I have paid much more for insurance than the actual car rental. Taking the super CDW paid off in Netherlands last year. Do not double book. You can always go to the next counter, or plug into the internet. It used to be cheaper booking from the US, but you might achieve that by going to the US site for a rental company. It's possible that you might pay some airport fees for pick up there instead of a city location: that will come out in your research of Europacar or Hertz or etc. Lots of discounts out there on the web, do a search, even with your airline or AAA/Costco memberships.
Take nice clear pictures of every part of your rent a car with the digital camera and make sure you look at the car in good daylight when you pick it up. Got a car in Paris once and about 9 miles down the freeway I noticed the left rearview window was smashed. Didn't want to turn around once that far away from downtown. Wasted mental energy on that trip wondering how much it was going to cost me for not noticing- turns out I was not charged. Brillant idea of returning a car in France in Nice, btw. Worthy.

If you are going to have the car for three weeks or more, do a lease through Peugeot or Renault. It has full CDW plus Millions in liability insurance and anyone in your family over 18 car drive it at no added cost. The car will be the model you ordered, it will be brand new and you can return it with as little fuel as you dare. A diesel is worth the extra money since they run great and the fuel economy is excellent. Do buy the GPS here with a Europe chip and you can learn how yo use it before you go but back it up with some good maps so you can track the big picture of where you are and where you are going. Do not double book whatever you do, there will be hell to pay if you don't show up. About the only excuse they will accept is a death in the family, preferably yours. Airlines, rental car companies and hotels have long ago run out of patience people who don't use their reservations.

1. Shop and take the best deal you can trust. You can get feedback about companies if you're not sure. 2. The drop off fee should be as they describe. We leased for a long trip, it had reasonable drop off fees. When I shopped rentals the drop off and CDW made leasing the better option. The biggest issue we had was finding the agent in the airport to return our car to. He wasn't where he was supposed to be, in true Italian fashion he insisted he had been waiting for us the entire hour we spent tracking him down. 3. As long as your reservation is to drop in Rome, you're fine. 4. No rental company guarantees the model (an advantage to leasing). I like telling the person at the counter what you need and why rather than being too concerned about the exact model. 5.. Yes, purchase a GPS here on Amazon that has both N.America and Europe maps. Learn to use it (including features) before you take it there. I'm torn here. I like TomToms better than Garmins, but the last TomTom I purchased (last year) didn't work. I should have sent it directly back to Amazon for a refund but instead sent it to TomTom to replace - they have now sent me the wrong model twice (plus refurbished rather than new device and no traffic, no updates - not even an initial update). Now I still need a Europe device and should go straight to Garmin but I don't think they work as well. 6. Something in writing would be nice. 7. I never double reserve and haven't had a problem.

We have used Gemut.com multiple times since 1991 to rent cars in Germany, Italy, and France. Bob Bestor and his son Andy provide excellent service. I like that they price-match, and also that you can cancel at any time without a penalty. Here is a link where you can get a free 16-page downloadable booklet all about renting cars in Europe. I highly recommend it. Best of luck! :)

Sorry, I forgot to include the link! http://www.gemut.com/car-rentals/free-rental-car-booklet.html :(