This is a subject I am studying because of my early 1950s Buick which I want to air condition.
I am considering creating a separate 12 Volt system just for the air conditioning, and leaving everything else as-is.
Your car will have plenty of power especially with a modern, high-efficiency compressor. You have to do three things to have a successful air conditioning project: turn the compressor; power the fans and the compressor clutch; cool the condenser and the engine.
Be sure you have enough current to power everything, and be sure you have enough fan and radiator and it is in good condition. I recommend an electric auxiliary fan, and maybe even a modern engine-driven fan with a thermal clutch and a shroud. This should give you a happy setup.

Bearing in the generator or water pump? Either can come and go.
Wheel bearing?

Hi, I'm new here but at the local Tractor Supply they have some graphite lubricant which might assist.
The springs should not squeak. Especially on a Twelve. You might end up having them professionally reworked.
I hope this helps.