Well this is shit. Personally I always wondered about this sort of problems and it's a common worry among people who have this sort of stuff... For example, let's say I have a game that costed me 400 dollars, something like Radiant Silvegun for the Saturn... if it gets damaged or stolen, how would you justify to the insurance company that it's a game worth 400 dollars and not a shit game for an obsolete console that should be worth 3 dollars?
You thikn they would insure my Commodore SX-64 for what's it's worth ? Defiintely NOT! so if it gets stuffed I'm fucke. Only solution is to somehow force them to accept the value of the machine when you sign up, wth a special clause or something. I don't know. But I really need to insurance some of my machines for when I go around on live performances, ad my kit would be hard to value.