The impact, learning and response in relation to insurance strategies can usually be discussed in the context of what 'insurability' actually means in a changing environment. Myself and Bill Riebsame reviewed much of the ideas and shortcomings of different research views of hurricane hazard mitigation and the feedbacks that are usually presumed to lead to adjustment. They of course always lead to adjustment on the flow-charts. As Neil Adger points out, a primary issue occurs in the debate as to the limits of pricing and discount rate applications in attempts to accurately incorporate losses.
Vulnerability is indeed cumulative.
This we termed a 'short-circuiting' of the human ecology framework to coin an 'engineering' phrase. It appears that we may not just need to know how we have dealt with past events but also how and where some past development strategies have failed to meet goals of equity or maintainence of local communities, and why some of these efforts to improve a particularly defined notion of welfare has increased the vulnerability of people and natural environments. An interesting field of research appears to be sprouting in terms of efforts to creatively integrate insurance and mitigation strategies. Hope this helps.