I’ve been playing with development in several of the mobile platforms over the last year, and for iOS in particular. Many developers are intimidated because of the differences between objective-c and other languages and the differences between cocoa touch and other frameworks. How to get started is one of the most common questions around.
First you’ll need an apple computer. There are some ways around this, but they are on the gray-side of the law and certainly outside of the OS X terms of use.
Next, you’ll need Xcode. Download it for free at https://developer.apple.com/xcode/. Xcode is the development environment for both OS X and iOS based applications. You can develop for free, and even test iOS apps in a simulator. If you join the iOS developer program, for $99 / year you can deploy to devices (up to 100) for testing purposes. You can sign up for the program at the iOS portal, which also hosts all kinds of tutorials and guides available to members and non-members.
Apple just recently posted this a getting started guide that will walk you through the basics. They have many other great docs available on the iOS developer site, including this objective-c primer and a longer version here.
I recommend The Big Nerd Ranch Guide for iOS. Among the iOS developers I know, it’s considered the best book to start with.
And for troubleshooting, no post about iOS would be complete without mentioning stackoverflow. It is the best site for any programming question, not just iOS / objective-c questions.
If you take the time to use the resources available, and work with (not against) the platform and supporting guidance, I think you’ll find iOS to be a friendlier platform than it’s reputation would suggest.