Updates are critical to me, too, but also filesystem access.
I wavered when switching from iOS the first time, I really did, but it was jailbreak carousel or "no files for you." iPhone's data model was light years ahead of other mobile devices when iOS was launched, but now it is a noose around the iOS neck.
On Android, root and filesystem access are much easier to get and maintain, and many, many more apps acknowledge the existence of files. I'm not a huge fan of managing my own updates—I'd rather have OTA—but I can do it when jailbreaking is the alternative. I refuse to use any device that doesn't give me filesystem access to work with data.
iOS is still powerful, esp. given some of its apps. For writers, Daedalus and Ulysses; for lightweight databases, TapForms or Ninox, etc.; for personal information management, DevonThink to Go. And of course there are excellent options for artists, videographers, musicians, etc. There is no equivalent to these in the Android space.
I don't have to do the art/music stuff, though, and so I'm not as tied to iOS as some. I recently tried to switch back with an iPad to be able to use TapForms, Ulysses, and DevonThink (I use all of them in my Mac OS space). I couldn't stay. Maintaining jailbreak was a massive PITA, and on top of that, the experience sucked. iOS right now is laggier, harder to use, more crashy, app-by-app, and has zero customization. It's also damned hard to sync local stuff on and off (images, music, files, etc) because iTunes is craptacular and getting worse.
On my Android devices, I plug them into USB, have USB mass storage support, copy the files over, and then can open them in any app that I please. For a work device that needs to quickly onboard and access, say, two dozen files that are a mix of Excel sheets, Word docs, and images, that workflow is head and shoulders above what iOS currently offers, even with jailbreak.
Yes, you can do the cloud thing, but then (a) you have to wait for sync and trust that it worked, then open each file one-by-one to localize (i.e. download) it using the cloud viewer app (e.g. Dropbox), then (b) hope that the app you need will be in the menu to let you open it. Eight times out of ten, maybe more, it won't.
I was sitting there one night using wget to pull files down from my own web server that I needed to access, then going into local application folders to and editing configuration files with vi to "onboard" them into the app on the iPad. Then I thought, "What am I doing?" and I logged on and bought a Galaxy Tab S then and there. Two days later it arrived, I ROMed+rooted (took about 20 minutes) and I'm back to my old workflow again.
iOS is a dream for lightweight consumer use. But for doing work—which (if you watch the original keynote) is how it was pitched—it is now behind the curve. But it's still 100,000x better than Palm or Blackjack back in the day. That was a nightmare. Even if you were totally wedded to your device for work, you always felt like "it's just not worth it" and "why am I even doing this, gaaaaah!?"
Those devices, which were state of the art just a year or two before iPhone, became laughable at the iPhone's release. Like, completely laughable. I still have a Palm 6xx somewhere around here. I stumbled across it and powered it up a while back. It's like using a mechanical typewriter vs. a Macbook Pro.