Nexus 5: Safe to update to Lollipop if on rooted + TWRP Android 4.4.4?
The answer is the update won't push through if you have a custom recovery like TWRP. I had to restore the stock recovery using the Nexus Root Toolkit. Then the update showed again, and it went through flawlessly. Even the re-rooting part (again using NRT) was perfect.