David,
Thanks for sharing your experiences; I understand that there are a variety of functional groups, and perhaps I am just too much of the wild-eyed dreamer.
On the other hand, I have seen seen the same type company run completely differently, so I wonder how much is architecture via social engineering since most folks come from other insurance companies, and so that is what they build and expect.
So I won't by any means minimize the challenges, but I think that, at the very least as a thought-experiment, it is a worthwhile endeavor.
Who knows better how to make an un-insurance company than the folks who have to deal with them all the time?