Such limits...
Oh well. I shall stick to what I've already got.
Handgun: S&W Mountain Gun.
Rifle: #4 Mk. 1* SMLE
Ottomobooble: '82 Porsche 928 4.5 litre.
Guns are guns, and are pretty interchangeable. Handgun calibers must start with a 4, however, as handguns are by definition underpowered, and therefor neccessitate big holes. Semi-autos have an ureliability potential (Percieved only in an intellectual capacity, granted.) that I prefer to avoid, so I'll stick to a rifle that demonstrated service-ability through two world wars. I'll admit this is somewhat simplistic thinking, but one must refine drastically restricted choices down to essentials. This means thinking up reasons to disqualify entire classes of good choices, rather than weighing reasons to keep various styles. "Carving hippos, rather than peeling potatoes", to coin a phrase.
The car is a different matter. Ownership of the Porsche has utterly ruined any hope of acceptance of any American car by the likes of me. Having crawled up inside of examples of both breeds, I'm sorry to say that American cars simply do not compare. I'd much rather work on the Porsche, and the engineering seems to reflect so much LESS compromise for the sake of expense. (Later-model examples could perhaps challenge this opinion, but I lack experience with those, and I can only stick with what I know.)