You offer bets with quite good returns (depending on the amount these shares are priced) and I think I can sell to myself on GLBSE, so all in all you offer quite some incentives to crash some mining bonds and earn money with it.
Howto:
Buy all "tails" shares you can afford.
In the end of the month, borrow shares of one of the index bonds (the one with the least bids ideally).
Sell bonds right before the last time the index is calculated, mostly to yourself (bid a lot of shares for 100 Satoshis or so, to keep fees low) and a dozen or so to some lucky ppl. You can even sell multiple times, for more shares traded (I REALLY have to test this out on some trash shares with the API! Might be interesting to have a few thousand shares traded + no fees(?), if you sell for 1 Satoshi...)
It might be the case that you manage to crash the bond even after that for some time, so you can cheaply buy back the missing shares and return them to your lender.
Congratulations, you crashed the index (shares trading for a few satoshis should have some impact on it, no matter how you calculate the average) and win the jackpot!
Your bets can only work if it is as easy to manipulate the price up (or to just buy through the walls) - as there is no real incentive to keep up lots of empty bids but it is completely free to put up ask orders just in case someone really wants an asset I hold so badly that he'll pay a huge premium (I recently sold 1 share of TEEK.B for 1.2...) as I get dividends in the mean time anyways, it is always VERY easy to dump share prices with tiny amounts of shares.
Counter tactics would include allowing open orders that are not 100% backed or simply building sniper bots that detect rapid down movements and that jump in the middle, bidding themselves and getting a few cheap shares. The difficulty is then to make sure these are really just cheap shares, not already worthless shares that someone else wanted to get rid of.