The insurance or the training? There's a lot of good training available currently. Outside of basic classes I'm not sure that I would point anyone towards the NRA for training. On the insurance side, it's not quite the same thing but I've been a member of the Armed Citizens Legal Defense Network for several years now. I like how they operate and the quality of people they associate with (or rather those who choose to associate with them). Without going down that rabbit hole as it might lead to adult discussions that I don't believe are allowed here anymore, I don't trust the NRA not to step on it's own dick when it comes to even the simplest of things. It has proven time and again that self preservation is it's number one priority with everything else a far second. An 800 pound gorilla, but one that doesn't know how to or is unwilling to use its mass except to continue being fed, if you will. I think things are changing within the organization now, but like turning an old, giant ship, it will not happen quickly. You can also search for write ups of the NRA's treatment of it's long time partner USCCA as it rolled out it's Carry Guard program. There's some interesting stuff there if it's still available online.
More for the insurance... thanks for the info. This is exactly the sort of response I was looking for.
I researched this one and Carry Guard and ended up going with this this one. Seems to be a better plan overall.