I think it is a risk/reward situation.
I am speculating you want to fly in to inspect the car so you don't buy 'sight unseen' which is good. But what really are you gonna be checking for that you haven't seen in pictures? Probably noises, knocks, and drips. Hypothetically, if you see something you don't like, are you prepared to walk away and pay 'short notice' price for a flight back and a night in a hotel? If you do break down on way back, what will be cost of towing, cost of Mechanic (assuming the repair cannot be done by yourself), the hotel costs for waiting to get a part you need (In case you break down in a town that doesn't have parts for an 80's car in stock). Plus gas, mileage, and wear and tear. I mean a blown tire could be an additional $300 if it cant be repaired. To me that is a lot of risk $$$ wise. I am guessing this is a cost saving maneuver so $$$ is a factor. I have dreams of taking my GN on a Route 66 tour but those are always set in the springtime hehe. I dunno of anyone who thinks of doing a winter cross country tour. Come to think of it does the current owner use antifreeze or just distilled water? That could ruin your day if you stop overnight someplace.
Searching on this site you will find folks that have had success and failure on trips. Most problems come upon you without warning. Not knowing the history of the car adds to the risk. Knowing what is a normal noise vs one that indicates a problem comes with time or a trained ear. All of our cars run great until the day they don't, nobody plans a breakdown, and Tools may not help without parts. You might be able to get the car to limp home, but if home is 700 miles away it may be to much to ask. AAA is gonna be the most valuable thing you can have on your journey.
If you have a feeling of trust with the seller, I would make a deal contingent on inspection, then get someone from the board to check out the car for you or with you. Odds are they already have a car they love and aren't gonna snipe you and buy the car you want. If the seller was worthy of your trust, he wouldn't do that anyway. (and if he didn't honor his word on the deal, could you believe his word on the condition of the car?)If the inspection comes back okay, I would have the car transported using the best method you can afford. Obviously covered is preferred, but if you are willing to drive it all that way, I am guessing you aren't concerned about salt or rock chips so even uncovered would be fine.
In my opinion, at the end of the day, the car is either gonna be either as awesome as you are lead to believe it is, meaning it would survive the drive, or it will be a time bomb. (Though I think many of us say these are time bombs and it is just a matter of what the clock is set to hehe). Your only chance to find our before you spend your money is to have someone who fixes these look at the car, but even then it is no guarantee.
But even if this car turns out to be a lemon, I think it is better that you find out at your house in CO rather than somewhere along the way.
I think the most solid advice is a round trip ticket, inspection with a board member, and enclosed shipping. I hope you take this next sentence with an air of helpfulness (cause that is how i intend it). If $$$ is the reason you cannot take that advice, please consider if you have $$$ to save yourself from the side of the road. A tow from Iowa is gonna be much more expensive than uncovered shipping, and you don't have to freeze to take advantage of it.
Good Luck and Safe journey. I hope your start to your ownership is a happy one!
