Dkelley are you still having problems putting your logo's in the game?
I couldn't get them to load in either until I switched from iExplorer to iFunbox.
Here is what I did!
* Started new game and created a save file quit the game and closed the app
* Loaded up iFunbox and went into the following location saved_games/Game 1.lg/news/html/images
* Copy logo's from PC (Before copying the files across make sure that the team names & nicknames appear correctly on your save game and on your logo's)
* Start iOOTP 14 and enjoy this great game!
I hope this helps!