9.9999 times out of ten, if a vehicle and bicycle collide, and the cyclist has half a head on their shoulders, the vehicle's insurance will pay (and more than likely, the cyclist gets their fair share of pain). Since I have more that half a head on my shoulders, I have no worries about "being at fault" in an accident. Pedistrians are another story, but in almost 18 years of cycling, I have never hit someone on my bike. If that were to be the case, I have an umbrella policy equal to my assets.

One should be cautious about filing such a relatively small claim on the homeowner's insurance. I am confident that they would "pay" for their claim many times over in the form of increased premiums. My most expensive bike (~$4000) isn't used for city riding and isn't left on the street locked up to a rack. My $300 motobecane does just fine on the streets and I have very little worries leaving it locked up anywhere.

All this said, have you talked to an agent to figure out the specifics of your policies? I've found the more I learn about insurance, the more "risks" I am willing to take in some areas, such as cycling. And that you are double covered in other areas like medical. And I certainly hope I don't ever have to make claim on my life insurance!