OK, all of my Oaks are connecting to particle.io. I realized the "No user rom" simply meant that I hadn't uploaded a sketch.
I replaced the oak cli in ~/.arduino15/packages/digistump/tools/oakcli/0.9.3 with the one I built that fixed the file name thing.
I uploaded to Larry (my oaks are Larry, Moe, and Curley). COOL! It works as expected. I run cli to select Moe, upload the sketch, and it goes to Larry. Hmm..... I run the cli to select Curley. Verify that .oak/config.json points to Curley, hit upload and the sketch goes to Larry. Same behavior when I try to upload using the oak cli instead of the Arduino IDE.
I power off (unplug from power!) Larry, since I am thinking that he may be seizing the connection. No my uploads fail.
Where is this getting cached? I see all three devices, no I know that particle.io knows about them. I have verified that .oak/config.json points to the correct location.
Any suggestions?