At 18 years old, probably time to replace the lights.
I'm going to go with that thought. But I am still a bit disappointed (LOL).
The progress today, I've determined that the spa light, which is about 15 feet away, is in the large (red line) conduit! Yes, you definitely want to make it easy to pull through for that one.
The pool light, in the deep end, about 50 feet or so away, is in the small (orange line) conduit! Yes, 50 feet of nightmare trying to pull a huge wire through a small conduit. Leaving me with the other thought, why not use the same size conduit for both? Of course, that would have cost $1.82 more. But beyond that, I'm wondering, is it possible that the pool light, at 50 feet, came up just those few feet short? And thus as nobody would notice for many years, the worker just spliced onto the cord? Either way, nothing in that small conduit is moving, either from pushing at the light or pulling at the junction box. I'm not really sure how much force can be used for pulling, but at the moment it seems pretty immovable in the conduit.

The last bizarre aspect, the very large external green grounding wire, it's in the large (red line) conduit. The wire in the small (orange line) conduit has no external grounding wire in it, despite there being both a grounding wire and the light cord coming out at the deep end pool light. I'd swear that it is the same wire going from the large (red line) conduit to the deep end pool light. I keep thinking that there must be a way to test the wire, but I also noticed for the spa light, there are two green grounding wires, I guess one in, one out, but to me both of them look much smaller than the green one at the junction box.