Hey Beno,
I am 99 percent certain that the root of all (or at least most) of these intermittent problems that are being reported is from excessive ripple on the DL's fast charge circuit for the iPad when it goes into constant current mode. This causes random USB data errors and random problems. If you want a way to reliably reproduce it, run your iPad down to 20 percent and then start testing. Or better yet, find an iPad with an old faded battery, and it will likely stay on fast charge the whole time (so you dont have to worry about the DL charging it up and then the problem goes away)
If you can post (or PM me) a schematic of the DL's iPad charging circuit with the part numbers for the regulator chip and associated components (inductor, output cap, freq divider, etc), I can probably tell you what the problem is and give you a field mod. If you want to compensate me for the effort, I could probably turn it around in a couple days (no guarantees, depends on what we're starting with here, but I have some familiarity with similar circuits and the problems that they can cause). I understand from WK154 that the analog section where this circuit is located is a PIA to get to, so if you have any suggestions on how to get to these parts with minimal fuss, (or a service manual if one exists for the DL) that would be appreciated.