Other than that, I really haven't run into issues I couldn't figure out via Stackoverflow or Apple's docs/samples.
The real issue for me was wrapping my head around the frameworks and understanding how it differs from Rails/web world. You might find it helpful to just take a week off and bury yourself in it. Try and pick a very simple (but useful/functional) app you can build and ship in a couple weeks. Give yourself a deadline and do it.
Also, storyboards are really powerful and can save you a lot of time once you learn them.
I'm mostly a Rails/Ruby dev as well but am doing more iOS. My recommended resources are:
1. BIG Nerd Ranch book (best book IMO) http://www.amazon.com/iOS-Programming-Ranch-Guide-Guides/dp/...
2. Programming iOS (5|6) by Neuburg (either version is fine) http://www.amazon.com/Programming-iOS-6-Matt-Neuburg/dp/1449...
3. Ray Wenderlich blog and tutorials bundle (worth the money) http://www.raywenderlich.com/store/ios-5-and-ios-6-by-tutori... His storyboard tutorials are great
4. NSScreencast (think RailsCasts for iOS. Not as thorough yet, but worth the money) http://nsscreencast.com/
5. Do a week-long, in person class such as http://pragmaticstudio.com/ios if you can afford it
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Other than that, I really haven't run into issues I couldn't figure out via Stackoverflow or Apple's docs/samples.
The real issue for me was wrapping my head around the frameworks and understanding how it differs from Rails/web world. You might find it helpful to just take a week off and bury yourself in it. Try and pick a very simple (but useful/functional) app you can build and ship in a couple weeks. Give yourself a deadline and do it.