As much as I like the simplicity of the old cars ( I have a 1960 T-Bird ) If you plan to make it a daily driver transplanting a modern EFI system is not a bad idea.
If the engine configuration is similar to one that exists and is EFI already then you have it easier. If you have a flat plane boxer 8 you are going to have to do a lot more work. Your Chevy V8 is common and virtually identical mechanically to modern engines.
If you want to go heavily DIY, go megasquirt.
With my particular knowledge I'd adapt a Ford V8 EEC-V EFI unit to it and run direct spark fuel injection via MAF. You would need to do a bunch of fab work unless you can find an EFI manifold for the engine to fit the injectors and MAF sensors. Adding a crank trigger wheel and cam trigger is relatively easy, a bit of welding and possibly a modified pulley or 2. Adding HEGOs is easy as are the balance of the sensors, IAT, ECT, TPS.
Use a Tweecer or Moates piggyback unit and reprogram the ECU to operate the sensors and outputs you have and you will now have a closed loop, much more efficient and possibly more powerful engine.
If you are brave and smart, add knock sensors in the cam valley and go for dynamic timing, it will tune for the fuel you give it.
Still though, just rewiring it and using modern electronic gauges behind the original cluster faces would be nice...
I'm keeping the 1960 T-Bird original, it only has 62k miles...