How can I synchronize everything with one solution?

Hi! My boss has like 5 computers, iPads, iPhones, etc. Lots of devices. He wants “everything everywhere at all times.” Photos, documents (Word, Excel, Powerpoint), music, etc. I don’t think iCloud can do it all in an automated way that solves all of the issues, though it does seem that this is an opportunity for a “cloud solution.” Also, he isn’t very organized, so an application that forces him to be more orderly would be good. I am not really looking for a free solution here, I am looking for what works. Does such a beast exist?