318
360
No different than an A body- anything from a slant to a 360.
318/360. Single cabs were available with slant and V 6s, so a smallblock is no issue, even with "towing once or twice".
Hell yes. I pull a 16' camper, a 14' boat, and a 10' utility trailer with my '66 Dart wagon. I wouldn't hesitate one minute, as long as the vehicle is set up properly to tow. I've got a custom receiver hitch, load equalizers and an electric brake controller- all common stuff you'd need for towing with any car.
The stuff you're talking about here isn't so much a matter of engine size, you're better off worrying about rear end gearing. Bigger, heavier cars could navigate traffic just fine with a 273 if it's geared right and running good. Something around a 3.23/3.55 and a good running small block (even a slanty) of any size will be just fine for navigating daily traffic and accelerating up onramps and through intersections. Just remember that as your gears go up (numerically) you'll gain torque, but you'll decrease your mileage and increase RPMs at highway speeds.