I've been thinking about this for about twelve hours now. My initial answer was of course, why not, but then I realized 500 feet is really high. For the vast majority of that distance a fall would kill you, and even if my chance of falling is only 1% (which seems generously low considering my coordination), I value my own life at more than $50,000. Logically that's also proportional, given that the increasing chance of lethality is roughly linear and the payment is linear. But obviously I am willing to climb ladders some distance, seeing as I've climbed less safe things for free. It kinda depends on the type of ladder and also how I'd be getting down, but I think under normal circumstances I could be enticed to climb a 30-foot ladder if I didn't have to worry about it toppling over, or about three storeys. But the money compared to the risk of lethality doesn't really convince me to go out of that comfort zone.