Custom Car pulling an old Airstream = Bad Idea?

Once some crazy idea gets stuck in there, I cannot get that thought (no matter how stupid) out my head… OK, here’s the deal: I really want a vintage (late 50s or early 60s era) Airstream trailer to take the family for some overnight camping, road trips, etc. Even more so, I want to pull it behind my fairly stock ’57 Pontiac Safari wagon… Bad idea? I know I’ll probably need to seriously upgrade my wagon’s brakes, maybe add a transmission cooler for the HydraMatic? All the old photos show some gargantuan 24 foot Airstream being pulled by regular passenger cars, so I’m guessing my big 347 c.i. V8-powered Poncho should be able to hang with a 2,200 pound-ish 18′ or 19′ trailer, right? the wagon is essentially the same as an old light duty truck with the boxed frame construction.

Let me know your thoughts, and more importantly, let me see your old car pulling an Airstream!