My hang up is the theoretical multi-state road trip. I wouldn't leave without doing a brake job if needed. I'm talking about breakdown potential and severity. Let's take a car and assume it's all sorted out, EFI or carb, and poop hits the fan with your fuel system.
Potentials-
EFI: In-tank fuel pump, 10 micron and 100 micron filters, regulator, ECU. All of this is a few days in the mail. Definite flatbed service and a disruption to a trip.
Carb: Fuel pickup, fuel pump, filter. At a parts store or one that's near. These are also cheap enough to carry a spare along with a small parts and tool kit.
Carb issues can be slower in stopping you in your tracks than EFI's often sudden stoppage or non-start issue.
Either way, to do what you want to do either a carb or EFI will do it. Some worthwhile advice has been given. Engine swap to a modern engine platform(most likely with EFI), run natural gas or an ethanol blend, overdrive transmission, and the catalytic convertors and you will be doing as good as you CAN do. Look through
Muscle Car Solutions content for EFI vs Carb, tuning for both, and understanding it all.