"Is it worth the time and hassle? Only you can answer that for yourself."
No. Absolutley not. The little sys admin work I have to do at work is all that I want to. I trust Apple and Google with all my stuff -- icloud storage, passwords, Google for email, etc. It just works, and I can move on with my life and focus on things of value to me instead of worrying about an upgrade blowing things up, security patching, backups, etc.