The richest man in the world (Bill Gates) famously had to watch his attempt to import a Porsche 959 sit in Seattle Customs impound for about 10 years before he could get it. There is now a loophole for "historically/technologically significant vehicles," but don't think that any car that isn't extremely rare or with a significant documented pedigree will qualify. Looking for 25+ year old cars to import is the easiest route, although none of them come Apple Carplay from the factory.
At one point, BBC was auctioning off their Top Gear "reasonably priced car." I actually thought about bidding, but was afraid that appearing for several seasons on the most-watched TV show in the world and being driven by dozens of famous people would not be enough pedigree to import it to the USA.....