Similar experience here. I use iPhone, MBP and iPad. Originally thought that having everything under one umbrella would be a huge help, but the reality is the syncing is such a pain that I never do it. Took me many, many months to even get AirDrop working between my own devices. iTunes is very frustrating to use in managing iOS devices.

one of the things that apple didn't pointed out is that there are 2 versions of airdrop. i didn't know this and had an older version of osx that wouldn't sync with my iphone. no error message either.