I always take the CDW at Enterprise because I rent for short periods of time and can't be bothered worrying about somebody dinging a door in a parking lot and then having to deal with the rental company. If it is dinged, bumped, etc I just return it and never hear anything. I agree that the rep by the car will try to upsell the CDW, but since I take it anyway that isn't an unpleasant experience.
For expense account types who rent cars a lot, I agree that Hertz Gold is great - at some busy U.S. airports one can wait 40 minutes in line at the counter to do the paperwork to pick up a car. I waited almost an hour in line at LAX once with Avis. With Hertz Gold club you just get dropped right by the car and off you go. I've travelled with someone who is a Hertz Gold club member and this program saves a lot of time at the busier airports.
For expense account types who rent cars a lot, I agree that Hertz Gold is great - at some busy U.S. airports one can wait 40 minutes in line at the counter to do the paperwork to pick up a car. I waited almost an hour in line at LAX once with Avis. With Hertz Gold club you just get dropped right by the car and off you go. I've travelled with someone who is a Hertz Gold club member and this program saves a lot of time at the busier airports.