So I did another look at insurance. As I was experimenting in a Myrmidon on the lowbie toon in a storyline combat mission, I had completely forgotten about "orbiting" and was flying the BC in the combat mission like a parked BS in an Incursion. Not an entirely clever strategy, especially in a toon with high indy skills and relatively low or non-existent combat and core skills. Surprise, surprise, the Myrmidon popped. This wasn't one of those "way in over your head" scenarios either, as the boat had dual reppers, AB and 4 active hardeners, so it was taking a while to die, but somehow I thought that as the rats popped, the incoming DPS would drop enough that the dual staggered reppers would slowly claw things back. I hate running away, and that means I usually wait too long, and then can't run away in anything but a pod.
Anyway, about the insurance. Keeping a rough tally of the build cost of the Myrmidon, it was just under the 30 million mark. About 20 for the boat and 10 million for the mods, rigs, ammo and drones. The first BC that popped wasn't insured. The "no insurance " insurance payout was about 7.5 million. To insure the boat for the best policy was also about 7.5 million, and the payout is almost 29 million. Total boat cost is ~37 million with insurance, so the net insurance return on its loss is 22 million, and a net loss of about 9 million. If the boat wasn't insured at all, it would still be the ~30 million cost, minus the 7.5 million "un-insurance", for a net loss of about 22.5 million. If I do insure it, don't lose it until after the insurance runs out, and don't insure it a second time, then the net loss is back to about the original cost of the boat, 30 million.
Now, if I was a hard core pvper, I'd likely insure everything I undocked in. It'd still be a money-losing venture, but not as bad as no insurance at all, obviously. In my current PVE Eve universe though, I guess the only boats it's worth considering insuring are the combat boats. The Hulks and Macs have paid for themselves multiple times and the risk of losing them is very low. Same with the transports. I'm not too worried about frigates, but I guess for battlecruisers and battleships, I'll likely insure them at least initially. The bonus with Incursion boats, is that if you lose an armor incursion boat in an Incursion site, the crew from TDF and BTL will reimburse you up to 500 million. Where, how and why? Well, the money they make from auctioning off the MOM site drops goes towards a ship replacement fund, and as people don't seem to lose too many ships anymore, the fund is fairly flush with cash.
The Point? If a ship is likely to be lost to misadventure, I guess it's worth it to insure the boat initially. After that though, I likely won't insure it again.