It seems like these days there is insurance for everything, you name the situation, and some company has drafted up a policy that will save you money IF something happens. 
As a pet owner we are all forced to deal with the decision on whether to get insurance for our pets. If you are like me, you tend to look at ALL insurance options with some amount of skepticism, especially given the capitalistic nature most insurance companies operate with. It would be nice to think these companies are looking out for our best interest, but we all know better than that.
We have done some research on the topic and have found a few articles that provide good insight on what to think about when making the pet insurance decision.
http://dogtime.com/pet-insurance.html
http://www.consumerreports.org/pets/0307vet2.html
http://articles.moneycentral.msn.com/Insurance/AssessYourNeeds/ShouldYouBuyPetInsurance.aspx?page=1
We hope this information has been helpful!
The Jack Barklaus Foundation - Pet Blog 
Hey Chris~! Aaron forwarded me your page and I was so happy for your efforts. My Mom runs a rescue operation that takes dogs and cats from death row at high kill Animal Controls in rural Indiana and finds them spots at non-kill shelters and fosters across the chicago area every week. We are big advocates for adoption.
Anyways, thats not why I was writing- I wanted to comment on your post because we recently got VPI insurance for our cats at the recommendation of my vet. We decided to do this because last year one of our pets got very sick with an auto-immune disease and I am embarrassed to say how much we spent out of pocket. If it had come in one lump sum, we may had made a different decision, but because it came spread out over 6 months we ended up hoping one more blood transfusion would be all she needed (did I mention she was only 2 yrs old!). Anyways, Bella did not make it and I vowed that we would never go through that again with out pet insurance. We have already filed one claim with VPI for a tooth extraction and they were very easy to work with.