too much when the guy hasn't posted part 3 yet, so I held back from writing a detailed reply. But in a nutshell, I have to agree with the other posters; players already take most of the risk here. What WildBill is proposing seems like an elaborate offshore bureacracy; a form of self-regulation that is unlikely to be adopted. While insurance is a nice idea, it essentially would amount to an additional tax on winnings. Players already pay between 2.5 and 4.5% vig on their total handle, making the game extremely tough to beat. Between vig, paying for picks, and insurance, the average schmoe would never win a nickel.
The reality is that this is a young industry and still 'shaking out', just like autos, phones, ISP's, etc. have historically done. First there are thousands of businesses, and eventually there are a few, mostly solid players. The difference here is that the players are to some extent not just customers, but "investors" via their postup, and thus they are exposed to risk which customers who buy autos, ISP service, etc., aren't necessarily in for.
I find it likely that books will reject this insurance notion; a bad book of course might see it as another potential profit center or a way to keep the ponzi scheme going; a good book will say "We don't need it, we're as solid as the day is long".
Recently I posted elsewhere on this forum that your best bet offshore is to stay informed and don't treat the Rx or others as "watchdogs", they are informational only. Don't rely on anyone else to think for you or choose for you, or even to 'insure' you; do as much investigating as you can when you choose a book and play it cautious. If you are chasing bonus rainbows and get burned, you have only yourself to blame.
Shifting risk via insurance is mainly a game that benefits insurers (ever been in one of their plush offices? They have to do something with all that spare cash of yours they are sitting upon). I don't see this plan happening but I will read part 3 anyway