Thanks to Nordic and their social media outreach programs, I won one of the official dev boards (for the nRF52, my target platform). They even bundled a few sample chips. This will make my project much easier (and something to test on while waiting on PCBs and the like).

In the first iteration, I'm still planning on including the mbed HDK which includes the CMSIS-DAP debugger (including drag and drop programming), as well as making a small board to do that during the second iteration (when it's actually a watch form factor device). After all, I'm planning a small beta test, and the testers will need to be able to update the devices in case of bricking, or firmware fixes.