Ham radio is pretty easy. If I can get my Technician ticket just about anybody ought to be able to. And when SHTF most of the rules about how to behave when using amatur radio go out the window, per the FCC themselves.
Your “emergency radio” (the one with the hand crank) probably has a few ham bands so you can listen and get a feel of what goes on. There are reliable handi-talkies that will not run you $100 each – or go to a Ham Fest and pick up some used ones for maybe 25% of MSRP. At the same time you can try out talking on the radio and ask lots of questions – like where are the repeaters in your areas and what frequencies they are on, as well as just how the heck do you program that handi-talkie you just bought.