re: Least expensive way to add low-level lighting to this cluster

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Voltage drop not being the problem, current is.

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I use them interchangeably even though I know better.

I don’t think you need to worry as long as you don’t put too many lights on it. LEDs only pull like 3 watts per light, where halogen is like 20 watts. LEDs are pretty good at maintaining brightness, even if they aren’t getting exactly 12v. They also make multi tap transformers that allow some compensation for the drop.

You probably don’t want to hear this, but if I were doing it for myself or someone else I would cross the driveway 3 times, at the house and on each run (L and R driveway) and connect at the transformer.