I was having the same problem as MANY people here where having. My iPad would not charge in the stand. It would not always connect with other hardware that was attached. After going through hours/days of troubleshooting with SQUARE SUPPORT, I finally broke down and bought a new stand... that took care of the problem. *Charging* is working fine, and stand is connecting to register, printer & reader all of the time.

My Miura card reader also stopped working around the same time and had to be replaced. Not sure if it was related?  After spending about $300, to replace everything, hardware is all working again.