To expand on what morrow said, I would say that sharper is always better, but that there's different kinds of sharpness. And the kind of sharpness that is preferable depends on intended use. A highly polished, razor thin edge is great for making clean cuts in paper and cloth, and of course, for shaving. However, like morrow mentioned, a polished edge will just skip off the skin of a tomato, and other fruits and veggies (the obvious exception is onions, which sharper is better because there's less damage to the onion - meaning you cry less).
For tomatos, etc, a toothy edge with some bite to it will work better. A toothy edge will also perform better with cardboard and rope. A toothy edge will also hold up better over time with less maintenance because it's less likely to deform, roll, or micro-chip.
Personally, I prefer my edge somewhere inbetween, closer to a polished edge than a toothy one, but not too polished. I have 4 levels of grit on my Sharpmaker rods (diamond, medium, fine, and ultrafine), and I stick with the fine. I like a sharp, smooth edge with just a little bite. If I finish with the ultrafine, I feel it loses its bite; it'll shave arm hair easily, but it won't glide through paper.
In the end, it's all about preference and purpose. But regardless, a sharper knife will be safer than a duller one because it cuts easily and predictability. When it doesn't cut easily, you push harder, and if it doesn't cut predictably, you're on your way to the hospital. As for a knife cutting you easier, well, you probably did something stupid/careless in the first place, and in most cases (unless you really hurt yourself), a clean cut heals better than a ragged one.