My friend was shown pictures of the vehicle (a D110) and assured it would be in a container on the very next boat coming over.
There was some far-fetched scheme about swapping the VIN plates from a Ser. III onto a D110. The guy assured him this manouver would be just fine, no big deal. NOT TRUE! This, besides being totally illegal, was just sweet talk, the 110 never existed. Nor had the guy ever intended to actually ship it if it had.
The money was paid but the vehicle never came. After many months of excuses from the guy my friend was able to get some of the money back, but very little of it. There was no legal recourse for him either.
The authorities have figured for every permutation of import scams and for every tweaking of the regulations. They have seen it all. Semantics are of little interest to the US government. Whether the fellow you're purchasing from calls the vehicle a gift or not will, in my opinion, be of little concern. If I were you, I would make triple-sure that I have checked with the DMV, DOT, and the Dept. of Treasury after making sure the title is completely legit.
Once you mail the check to a different country there isn't going to be much you can do to get it back.
I'm not sure what state you will be registering the vehicle in. I know in my state, Michigan, when transferring a title in the case of a gift, only immediate family members are allowed a sales tax exemption. Documentation must be provided in support of such a relationship as well. If you're trying to avoid paying duties on the federal level this could very well come back to bite you on the state level.
My advice: just tell the truth. Don't call it a gift if it is not. Don't try to import the vehicle unless it is on completely legitimate grounds. It's not worth the trouble and hassle it can cost you. Even though the government seems like a big, lumbering beauracracy, too big to spend much time on the importation of a single vehicle, they have many agencies that are very capable in what they do and they WILL figure it out.
I think scam-artists are begining to realize the passion with which car enthusiasts operarte. People who love collectable vehicles, like us with our Cruisers, and my freind with Rovers, will often go to extreme lengths to acquire rare models. Because this often means going to other countries scammers can use borders as their protection. They know that once money crosses a border it become much harder for the scammed party to get it back.
All that being said, if you can work it all out, it would be a great Cruiser to have. Just make sure you can do it all legally and up front.
Keep us posted on how things turn out.