I worked for Enterprise Rent A Car for a couple of years. I was a top performer in South Florida and my suggestion was to always take the Damage Waiver if you were only using the car for one-three days and you didn’t have some type of credit card coverage (sometimes credit card companies are secondary to personal insurance… so I’d suggest Damage Waiver if they weren’t comfortable with that). If you were comfortable with the credit card coverage, my suggestion was to always get Supplemental Liability because companies NEVER cover the other car regardless of who’s at fault. But the reason I was successful at my job is because I would THOROUGHLY explain the procedure and consquences if an accident were to happen. Most people think that I was just a “salesman” but what they didn’t know was that I actually really cared about customers. I never tried forcing them to buy something I truly believed they didn’t need.