When I measure and count olive oil it is so high in points/calories that it makes me mad. I tend to undercount it as it's such a healthy food and Mediterranean peoples eat gallons of it without problems. I know they walk up cliffs all day but that's another matter. I am super-careful about what I count and try to use it both liberally and sparingly - liberally, meaning, often, and sparingly, meaning not too much on each food.
I use oil and vinegar dressing, but 1-2 tbs only, depending on the ratio. I count it as one point but it's probably 2. Since I don't use my all floater or exercise points usually it just doesn't matter.
I also always use olive oil and salt on veggies and generally count it as 1 point per cup. I do this for 4 reasons: 1. I like it and 2. the kids will eat their veggies that way and 3. I eat a very low-fat diet otherwise and 4. my diet seemed to be working so I left it as is. If I had hit a bad plateau maybe I would have considered changing my behavior.
One other really helpful tip - I got a bottle of olive oil from Trader Joe's that has a little dispenser nozzle attached to it. It makes the olive oil come out really slowly, and I think this helps when throwing it around a saute pan etc.
It is possible to measure out tablespoons of olive oil when cooking and keep better track that way. I considered this but only did it once or twice as I just tried to be conservative and as I said, things were working that way. But if you think you need to get a handle on your olive oil consumption then by all means, measure out some tablespoons for a few days when preparing dinner, salads, etc and see what you're actually using.
I did switch to making fried eggs with olive oil 'pam' instead of butter. They taste fine, and I eat usually 1 whole egg with extra white.