So, I've read through everything I could find on low voltage electrical code. It seems my installation is a class 2 circuit. The power supply is 100W with two 50W outputs, which conforms with class 2, and the wire splices are in a location where they're not subject to inadvertent physical stress.
I can't find any requirements for wire splices for class 2 needing to be inside a box, but I'm certainly not a NEC specialist. Anyone have any more insight?
Still, I like the idea of having the connector integrated in the fixture top. I may get a bunch of Molex or lustre connectors and design the top part so that the connector can be integrated into the fixture top itself