This strategy would also, if developed further, make legislative bodies impotent.
How so? If someone recieves money when their current business becomes illegal, this doesn't mean that they'll carry on in the business, ignoring the change in law. In fact, it makes it easier for them to cease their current business immediately.
I may be missing some major point, so if so clarify, but it seems to me that this would in no way decrease the effectiveness of legislation at discouraging actions after it was enforced: all it would do is decrease the effect of THREATENED legislation (that has not yet been passed).
Okay, my thinking is basically that the insurance mechanism's predicted effects feed back to the legislature-level, not necessarily the outlaw-level (though it can do that too -- see the end of this comment).
In other words, in anticipation of this insurance-like reallocation, a legislature will find most of its potential laws less appealing. For example, if they want to ban something, they are doing it to reward a politically-powerful group and punish one that is less so. They want, e.g. "lots of wodget-sellers jailed so that honorable wodget-avoide...