I hear ya. I am a kitesurfer and one of the hopes getting into this was shooting over water. But it is nerve racking. I guess you are either rich, ballsy, stupid, extremely confident or a little of all those. One answer I am looking into is using a glider like all the fpv guys use such as the skywalker. They can float, glide with a motor out, dont cost as much, can handle flying right into the wind with a slower stall speed. BUT you are limited to a damn gopro. I want to see when people start putting nex5n's in their foam gliders. more than possible. Hell, the avergae guy on here has got $4500 in the air at any one given time. It will always be less to put it in a plane. You just cant hover.
And I dont think Jeff is a good candidate as he part owns quadrocopter and can probably grab a new heli if things go bye bye. Just saying, he is a great pilot and photographer but it certainly doesnt hurt your confidence when there are more toys in the garage waiting to be "tested."