Replied. Basically, it doesn't ever seem like there's a problem to the user.. other than that the coins never show up in the receiving wallet. There are connections, the send process looks to complete just like all the other times, just nothing actually happens.
Not a bug with the app, just the stupid transaction fees. Basically, I was attempting to send something like 51 btc from 4 inputs to a single output and it was being rejected because I didn't include a fee. Instead, if I sent each of the input amounts separately, they were relayed successfully.
The fees are having the exact opposite of their intended results... a bunch of single, smaller transactions work vs 1 larger transaction that doesn't work.