I'm in NC and have a 998 that I've owned/modified for 5 years now.
Watch govplanet, earlier in the year they had M1097 HMMWV's and a few others for auction north of raleigh in Butner. They may have some come through again. The govplanet route I've used for a few items. It can be anywhere from weeks to 7 months in my experience to get something street legal in NC from govplanet as you need gov paperwork to clear, govplanet to generate an out of state title, then you go to the DMV and get it NC titled and licensed.
As another option look up Corey Walters @ KPJ military customs in lumberton, his business is on facebook. He always has some street legal ones ready to go and he is very honest and can go through them mechanically. He has some great options up for sale right now.
Insurance I have through Hagerty given its a 30 year old M998. Very good insurance and cost effective.
Depending on where you are some inspection stations refuse to see the HMMWV here in central NC. They are not supposed to refuse it, but they do. Mine turned 30 years old and is now inspection-free. For those less than 30 years old NC will require a basic safety inspection. You'll basically need to ensure mechanically the steering and suspension is in good shape, the lights all work including brights on the headlight, turnsignals, and add a license plate hold that can be tied into the rear marker light to illuminate it (buy a led one that can handle 24volts).