IMO go solar and forget all the wiring completely.

I have tried several and find it taxing on my recycle bin. Perhaps they have improved recently. I am willing to explore and will look into brands.

The good thing about solar lights is you can take them indoors during a power outage. During Hurricane Sandy, we would bring in the lights each evening and put them in big vases on each end table to read by. Then used them to light the way on the stairs at night. Did that for a week and it was priceless.

"Daisy chaining low voltage lighting advice"

You aren't really daisy-chaining the lights -- like Christmas lights -- so that if one fails they all fail, are you? You should be connecting them in parallel i.e., each one connects to the "landscape wires" independently. I would say that the clamp-on connectors would be fine if there aren't old cuts in the "landscape wire" casing that would expose the conductors to the elements. The Dryconn connectors are clever but you'd need slack in the landscape wires to be able to connect three wires (landscape wire in, fixture, landscape wire out) together inside one connector.

I hope you're using outside fixtures that follow dark sky guidelines.