I'd say it's a lot easier if you're working alone and have little costs. I have a small flat, and I don't have any employees. Also, I do the website myself, the customer service, the one or other ad campaign, the graphics, etc. So apart from my small rent and hardware (which is where I do invest, since I do think that good tools are really, really important) I have almost no expenses. Living in a small student town also helps since good and healthy food is really cheap here, too (like 3 eur for a solid and healthy lunch).
Seems Mac users have no problem paying for the software they use, considering that it's not overpriced crap that costs $60. But decently priced like $4.99
It may be a question of price, though I also think that it could be a bout ease of buying. With the App Store people really only have to click twice to buy something. On Windows if you need a product as a solution to a problem, you need to go to different websites, compare their offers, everybody has a different payment provider, then you have to download and install. Really, I think that for many people pirating is not only cheaper but also far easier. And, since usually only good software is pirated, and not the crap, you don't even have to do so much research and cognitive burden to decide which offer to take. Other people already did that for you when they decided which one to pirate.
There're also studies though, where people find out that Mac users seem to be more inclined to pay for software. Maybe it's a question of initial price: When I pay a lot of money for a really good meal, I don't mind spending another 5 bucks for a great wine to accompany the taste of the meal. So if you spend quite some money for good (or perceived good, I don't want a Apple vs. others flamewar here) hardware, you might also want to spend a bit more on software.
In most european countries, student's food is state subsidized, that explains the fantastic prices.
For example, you have no shortage of Windows text editors that are free. For the Mac your only real option is TextWrangler.
So I think VIM is not a good example of a good free Mac text editor.
You should qualify that with the demographics at your previous company. VIM (and Emacs) are perfectly good free editors for the Mac or any other platform.
It's probably best to start with a small project and tackle one project after the other.
I also read this book which helped since it tackled all the basics that one needs to know for a full Mac app. It's german only though (http://www.amazon.de/Objective-C-Cocoa-Nachfolger-Tiger-XCod...) alternatively the aforementioned Hillegas (http://www.amazon.com/Objective-C-Programming-Ranch-Guide-Gu...) which is really good.
'From C++ to Objective-C' is also good eBook. http://pierre.chachatelier.fr/programmation/fichiers/cpp-obj...
I also bought 'Cocoa Programming for Mac OS X' http://www.amazon.com/Cocoa-Programming-Mac-3rd-Edition/dp/0...
Cocoa is quite different than anything I had programmed before. Once I wrapped my head around nibs, IBOutlets and IBActions it was fairly easy. Once I got going, the apple developer docs were all I needed, but learning I found easier to do from a book than the docs.
If you already know how to program then this is a pretty great resource.
There are also some introductory articles to help you get started. For example: https://developer.apple.com/library/mac/#documentation/Gener...
But that's really it. I do have a non-app store licensed branch of InstaDesk that would work with a license file system, but I'm only keeping that alive in case the App Store becomes too draconian. Just so that I always have a way out. Though that's becoming more difficult now with the iCloud integration.
Hope that helps a bit.