Thank you so much for posting this! It was still helpful to me, almost 2 years later.
My son has an iPad Air 2 & it started doing this exact thing, so of course, I hit up the Internet to find a solution & found your post. Solved my problem then & a few times since. Not sure why this happens, but at least I have a solution now. It's not a quick fix, but at least I know I can get his iPad charging after he has let it die. Which he does often, even with more than one charger to use, even with a portable battery back up, at least once a month, his iPad will die & I use your method to reboot it and within a few hours it's charged back up.
I will say that I've never done the 3rd step 30-40 times, normally I do it 4-5 times & after the final reboot I let it go to the home screen, where it will tell me that I have 1% battery life left, then I hold down the power button & swipe the bar to power down the iPad correctly. Then it's good to go & will charge. This has happened 2-3 times, but with your instructions I can always get it rebooted and charging again. Ideally, my son knows not to let his iPad die, but he's only 10, so bad habits are not easily broken at that age.
Anyone else having this issue, the solution wildchild posted will work, it just takes time & you MUST power off the iPad while it charges after the fact, no playing with it while plugged in & charging which a lot of us do. It also takes your complete attention, you can't do this & let your mind wander, for it to work, you must devote 5-10 minutes to the task. You don't have a lot of time after the iPad starts up & then proceeds to reboot, so you HAVE to pay attention. As soon as you see the apple screen come up you have to be ready to hold the power button & home button to reboot the iPad & you need to do this several times, after which you let it start up & if you're lucky, you'll see you have 1-2% battery life. At this point, you hold the power button, swipe to power down the ipad normally & let it charge.
This does work & quite well actually, it just requires some time, effort & attention. Thanks Wildchild!