I roll the dice every time I lift off from home base. Engine failure on takeoff, between 30 and 1000 AGL, I have no good options. My philosophy on over water is that I will do it, just not all the time, and when I do, I try to get as high as I practicably can, even if I can't eliminate altogether the time I'll spend out of glide distance of the shore.
Now that I expect to be flying a few times between here and Vermont, I'm actually a little more concerned about flying over the Adirondacks than over, say, Lake Michigan. It's a remote wilderness about twice as wide as LM, with few airports, no chance in a light single of getting high enough to be able to glide to safety at all times, and no benign terrain to put down in. I'll still do it, but I really don't want to make a habit of it.