Well, considering I am rather new to the game (a little over 1 year), I have probably dropped somewhere near 250k in insurance (or more). My first experience with peerless was a community hunt to Grizzle. I burned through a rather tidy sum of cash in the opening stages gathering keys (probably 15-20 deaths) and then proceeded to die repeatedly at the hands of the beast himself. Finally, at the point the system told me I could not insure my items any longer, I realized my error and tucked my tail between my legs and skulked out of there. I lost everything that night, including the proverbial shirt-off-my-back. Thankfully, guildmates were kind enough to resupply me, and I keep a careful tab on my funds these days.