I am going to have a one way car rental that starts in either Germany or Switzerland. I know that cars "rented in Italy" can't use their credit card for CDW, but what about my situation? Anyone with experience doing this?

Check out www.autoeurope.com - they have the option to quote all-inclusive (eg zero deductible insurance) rates.
The cross border drop off fee for the one way rental is likely to be the biggest wildcard/cost adder to your rental.

Many people report that they have successfully used certain credit cards to cover insurance coverage in Italy, so I believe your blanket statement "can't" is not quite true. But since it would be a Germany or Switzerland based rental the rules for that country would apply - you are allowed to drive into Italy.

It's been a while since I rented in Germany other than corporate rental arranged by the company, so I don't personally know the current insurance coverage details with cc.

I am willing to pay the drop off fee, but would like to save on the hefty no deductible insurance fees. I have a Visa that covers everything, but unsure if it can be used.If a car is rented in Italy, you must choose CDW and can't use a credit card. I believe that's the only country in Europe with that rule.

Not quite sure what you mean by "hefty". On a recent trip to Italy our cost for a 5 passenger station wagon totaled $35 per day for a 2 week rental, zero-$ deductible included. Rented from Hertz, via AutoEurope.

What is a hefty CDW fee? Compared to the possible hassle of a claim if you need it? Compared to the cost of the one way drop off fee, plus any cross border fees they may charge. Compared to the total cost of your trip?

Don't forget you IDP for Italy. Oh no more expense.

Renting for 3 weeks and lowest cost deduct is around $250. This is from Expedia and their insurance is considered less desirable than my credit card's. Other options are quite a bit more (especially if covers everything).Drop off fee is crazy high, but is my only practical option. My question relates to the current law that says all cars rented in Italy must purchase a separate policy & not use Cr Cd.

You are not renting a car in Italy...
You are renting a car in Germany or Switzerland and driving it in Italy.

Don't rent via Expedia. Check out AutoEurope as suggested.

A hefty drop-off fee is never the only option. First off, forget renting from Expedia and look up AutoEurope. Second, figure out how to do two rentals, one for Germany/Switzerland and one for Italy. Take trains or fly between the two.

You might want to read this: https://www.autoeurope.com/travel-gu...tal-insurance/

Three weeks I'd at least price out the French lease offers.

That cost is only about $80 a week or $12 a day. I wouldn't call that so bad.

However, I don't understand the argument, Expedia doesn't force you to buy it, it's an optional add-on regardless. Even renting in Germany and dropping in Italy.

If you are traveling from one European country to another, take a train rather than pay a drop off fee. Once you arrive in the second country, rent your car there. Easier, less aggravating, and fewer pollutants fouling the air.

The pollutants fouling the air from a road trip from Germany to Italy are neglible compared to the pollutants fouling the air flying across the Atlantic twice.