Just after buying the Pencil, due to my use case detailed in point 2 of the side note in the question, I was getting the low battery message almost daily. Therefore, I searched the web for a way to get as close to a powered-off state in the Pencil as possible while it's not in use. Eventually I settled on going to Settings -> Bluetooth and unpairing the Pencil. When I needed to use it again, I just paired it again by taking out the cap and connecting its male Lightning connector to the female port in the iPad, then confirming the pairing when asked by the iPad. I tested this and it seems to hold charge much better. I could go a day or two without using the Pencil, and when connecting it again, it had lost no charge at all, or at most a couple percent. The main issue is that you have to remember to unpair it after use every single time. I realized my Pencil had died after a few weeks without using it, and it's not entirely impossible that I just forgot to unpair the Pencil at the time. The only solution I can think of, for now, to this issue is to add a reminder to check the Pencil's battery charge level every so often -- at least weekly, I'd say, and ideally daily if you don't find that too bothersome. It is my opinion, though, that an expensive device that dies after a few months, unless micromanaged as explained in this answer, is badly designed. I don't care how ugly an on-off switch is, if it means I don't have to replace it every few months (and pay out of pocket after the warranty expires.)