Android updating and backup is a shit show, no doubt. I'm a tech guy, root mine, and play with all sorts of custom roms, so I have no problem updating when I decide (and then going back if it sucks) but for average users it is awful. iOS is better for that (though not perfect).
For me, my pictures back up to Dropbox automatically, my text messages come through and are saved in Google Voice, my music and videos are all in the cloud, so it is really only app data that is an issue for me in terms of backup, and most of that (the important things) has cloud backups these days too. I think that is what Google expects for most people, which is why their manual backup options are so awful. Not a great move on their part but so it goes.
I tell people not to upgrade unless they are prepared for a factory reset immediately after, and even then I discourage it unless they REALLY want a specific feature or app. It just isn't really necessay most of the time. It sucks that that is my rec but it is: when you get a new phone in 2 years, it will have an updated version and you probably don't need it until then.
I love my Android phone and will never give it up. But with great freedom comes great bugginess.