FWIW, my dos centavos (oder zwei pfennige):
I lurked around on this site, g503, the craigslist and ebay boards, GP and elsewhere for about six months before deciding to buy.
Locally.
I looked at (and bid) for one sight unseen (I was about to pay a guy to drive two hours, inspect the truck for me and report back - he was also going to ship from Nashville to NoVA for about $900), and I lost the bid by $50. Or it went for $50 more than I was willing to pay which was about $17,500. I "looked at" sales all up and down the east coast.
Other HMMWVs in "similar" condition (meaning: some paint, cleaning up, good/new top/doors, rubber, CLEAN ON-ROAD TITLE and already tagged) were selling locally (mid-atlantic states) for at least that much and on up into the low twenties.
Sure, if you have a shop, a lot of time, do this sort of thing for a living, you can bid (read what some guys have gone through going that route), get a real gem for $8,000 or less and then spend the next year or two trying to get it roadworthy and have that "FORUO" stamp go away somehow - way I understand it several states are already voiding the roadworthiness and calling in the tags/registrations so it's still a gamble either way. So now you have a HMMWV parked on a lot somewhere that might need batteries, a transfer case, an engine, and you've got to get it off the lot in 24 hours and it's 800 miles away.
It can be messy, complicated, or, you can take your time, look into sales, salesmen (guy I bought from has sold umpteen dozen of the things, every Deuce bought by a certain local BBQ chain was through him and he's either a real straight-shooter, a good used car salesman or worse but I think I got a great deal from him all things considered), who's buying what from whom and WHAT ARE THE LOCAL LAWS governing inspection, registration, titling/tagging said vehicle.
Right now there's a handful of early 90s-type HMMWVs I see for sale on the evil auction site and on Steelsoldiers' and g503 classifieds for around $20k, some look better than others.
Since you asked, here's a suggestion: give it some time, look around, you'll find a better deal locally.
Norm