I bought a used AIH a couple years ago, my first custom. I was extremely nervous about buying a used bike as opposed to a new bike, bought a warranty, then ended up cancelling the warranty. There is almost nothing on these bikes that can break that will cost as much as the warranty price. Another guy on this site I ride with bought new, bought the warranty, also ended up canceling his warranty and getting the money back!!! With the deals you can get on used, you could buy used, ship it down to "bigdogtech01" and have him go through the bike, and still be money ahead.
My biggest fear was buying used, then having the motor grenade on me!!! But if you read this site, there's almost NO ONE who has had a motor grenade. Much more common to have a tranny or electrical problem!!!!! These problems are not nearly the cost, even though they can be more of a pain in the ass to diagnose.
If you were an army mechanic, I guarantee you this bike is within your skill level to work on!!! We are talking 1960's technology. I'm no mechanic, but grew up on a farm and worked with my hands. I had to take my transmission out of my bike and have it rebuild. I would never try and work on a bike transmission, looks too complicated to me, but after taking it out, there's not much out can't remove on these bikes in your garage with regular tools in an afternoon!!
On a sidenote, I lived in Davenport for 9 years and worked there as a cop for the DPD!!! There's some real good guys around that neck of the woods!!!