Cuddeback got back to me today. This makes much more sense as to why the picture count seemed so low before hitting the "overage".
"We also took a look at the connectivity on the account, and we are seeing situations where the cell device connects and transmits data but it times out due to insufficient cell service. When this happens the phone provider, in your case Verizon is counting the data received even though the transmission was never completed. When this happens, it causes the account to use data quickly and, in your case, caused you to go into overage even though you did not hit the 2000 photo mark."