Why do you think it's a pain? Mac is just unix and Android has a lot freedom with file managers and sync apps like desktop OS. I regularly move/sync files back and forth over WIFI between Android and Windows/unix. Look at Solid Explorer, Foldersync, etc. and also Autosync Google Drive/OneDrive for syncing via cloud.
I guess I am just used to my iPhone plugging in and iTunes doing the rest. Although the problem with iTunes was the limited amount of files it handles so the pain was in converting stuff. I could possibly be doing it wrong but after the first initial syncs are done it is okay for me. My entire music collection is on the device now and I use Airdroid which works fine.
I don't need to sync playlists and other stuff that often so it isn't an issue really. I have also been finding that as you said there are options. I was looking into syncing photos and noticed they were already there using photos from Google. One thing I did notice is it took forever to sync 60 GB of music the first time. More than 5 hours not sure if this is typical. Again none of the small issues I have had is tempting me to spend the money to go back to an iPhone.
It seems Android also out of the box requires you to look for the missing things you need. There seems to be a solution for just about anything you could desire. So while I am happy playing around and tweaking mine I wouldn't recommend my roommate switch as he uses his iPhone for work and doesn't want to tinker around.
I am looking forward to the release of two new phones at this stage. The next Edge update early next year and the Iphone in 2017. Nothing else would make me switch from the Edge right now. It is for me the best phone out there at this moment.
