Sounds like you've thought of everything, but consider this...
Samsungs are reportedly poor performers for reception. Doesn't matter how great a performer it is if it can't get a signal. I live in an area with poor signal and it works as well as any Motorola I've ever had, and that says a lot.
The Commando battery is tollerable if you do some things to help it. Mainly if you will disable the GZ apps and the VZW apps the battery life improves. Download an app that allows you to turn off the LTE radio (I use SWITCHIT-4GLTE) and keep it off unless you have a data intensive activity. That one thing will nearly double your battery life. Emails, texts, and MMS's work just fine on 3G, or 1xRTT (CDMA only) for that matter.
The extended battery is just ugly, no two ways about it. However, my phone is been on battery for over 14 hours and I have 80% left, so it's worth it and I'm still breaking in this new battery. With the LTE off I would imagine it would probably run for days.
About lockups and reboots... I can cause this with two applications - Solitaire (why, I do not know - it is a very small and simple app), and if I am watching a streaming video and I try to skip forward. Some seem to have more trouble than others, but I would imagine more often than not it is an incompatable app, and that happens to all androids. It is no where near as bad as the old Commando.
This is such a major improvement over the old Commando, and so far I have not had any missed calls, missed texts, or missed alarms because of problems with the software. It fits in my uniform shirt pocket and I can close the flap so it doesn't fall out, yet the screen is adequate size for viewing emails, texts, videos, etc. I do not worry about carrying it with me under my bunker gear, water from sweat or firefighting won't hurt it. I never carried my RAZR anywhere that I thought it might get wet, or dropped.
I have no response to the comment about insurance. Asurion is fairly expensive, up front and if you file a claim. I had a brick replaced by Asurion and they sent me a brand new phone with all the accessories. Obviously over time they will get refurbs to hand out, but I was suprised when this one came.
I will not be taking any updates unless others give good reports. Going from ICS to JB on my Droid RAZR did not make any improvement to performance, and actually hurt battery life.
Ultimately the choice is yours, and its a decision you will be stuck with for a couple of years so choose wisely.