Reflecting upon this wreck, I feel that this kind of insurance just can't be run in a big public company format because 1) the demand is too low (many posts itt testify for that), 2) ridiculous Skrill merchant fees eat most of the edge. I think one of the keys to success would be providing it privately, avoiding being flagged by Skrill as a merchant
To this end, I think
all-in insurance would be done better in small groups of people knowing and trusting each other, playing at similar stakes but different game types and sites (so poker sites wouldn't suspect collusion). Mutual trust has a benefit of reducing the transaction volume dramatically: instead of jerking funds on and off a merchant site, making it pay tons of fees and/or exhaust transaction limits, money can be sent once in several weeks in chunks of dozens of BIs when someone is in real trouble and longing for that refund. The transaction volume will fall because up- and downswings of the peers will cancel each other better.
Different payment processors can be used at once if the volume doesn't allow to use a single one without being flagged as a merchant, and also great use can be made of direct poker site transfers and 2+2 transfer threads. (There can still be a laundering investigation but it's easy to prove innocence as long as the transactions are played through and the mates don't gang up at the same tables.)
I see a couple of ways this can be done. Firstly, the friends can just agree to divide the total EV difference equally (or in some fair way) among them. It will reduce the AI variance by as many times as there are members in the group (btw, that's one of the main benefits of marriage to me
) to a negligible amount, don't forget about RIT as well.
Secondly, an insurance bankroll can be put up with fees for access to it like with InsuredPlay (it wouldn't last long without any fees - recall that any breakeven activity ends in a bustout almost surely sooner or later) that would get lower if the bankroll grew, but again it should be rather a small web of trust with members P2P'ing to each other (not necessarily through the bankroll holder) once in a while, more like a stable and with a full-blown staking-like contract and possibly 'registering' the relationships at a staking forum.