As far as free developer tools, I again don't know what is different from before. I hear you, but haven't experienced the nirvana you describe: I've been on Windows, where development tools have very often been free to play with and require payment to use them for real work.
The way I look at it is that Apple's gatekeeper role is appropriately minimal on OS X and appropriately strict on iOS, and for my part I trust the twain will never meet because of exactly that "general purpose computer" difference, but you have added some thought-provoking perspective.
Before, the process for shipping an app looked like:
1. Obtain Xcode, either as a free download, or from your OS install media. (Apple just shipped Xcode along with the OS for a while.)
2. Develop your app.
3. Distribute your app directly to customers.
With iOS, the process for shipping an app looks like:
1. Obtain Xcode as a free download.
2. Start developing app.
3. Realize you need to test on real hardware at some point. Before Xcode 7, testing on real hardware, even your own, cost $99/year. With Xcode 7 you can do it for free, as long as you get an account and have Xcode fetch the certificates for you.
4. Submit your app to Apple for distribution on the store. If you did step 3 without paying, then you need to pay your $99/year here.
5. Wait a week or so for Apple to review your app. With luck, they'll approve it. If they find something they don't like, they'll reject it and you get to go back and repeat this process until you appease them.
With the Mac today, you have a few choices. You can go through the App Store, where the process looks much like the iOS process, except you don't have to jump through any hoops to test on your own hardware. You can go through Developer ID, where the process looks like the old Mac way, except you pay $99/year to have a signing certificate. Or you can keep doing things the old way, at no cost, but most of your users will get scary, scary warnings when they try to run your software.
The thing is that it's not about the tools being paid, but the distribution being paid and restricted. I can completely understand paying for developer tools. Until they went crazy, I was happy to pay JetBrains for some of their tools, for example. Your Windows tools required payment to use them for real work, and that's fine. But if you didn't want to, you could have used mingw or something like that, and done everything for free and without restrictions. This option is simply not available on iOS, and is being slowly ratcheted down on the Mac.
To my mind, iOS security is where it needs to be for that device. I respect your opinion, but we're not going to agree on that. I've considered your argument and I don't see anything that changes the fundamental "so don't buy an iOS device, they do not have a monopoly and there are other fish in the sea". For my part, I'll keep buying them because I follow a similar philosophy that security changes are preeminent and should be allowed to break and constrain other software.
Thing is, if I believed the Mac was going to be ratcheted down to iOS levels of paternalistic control, I would be upset too. My conclusion is it'll never happen. I don't think they'll ever break their general purpose computer. If they did, you'd see a massive exodus of former Mac users looking for a new UNIX desktop. Maybe a big enough exodus to finally make The Year of the UNIX desktop happen. :)
The problem is this: what part of the process I described has anything to do with security? As far as I can tell, nothing. Apple's review process is pretty superficial and is entirely geared towards stuff like making sure nobody ships a browser that doesn't use WebKit, or an app that posts information about drone strikes. Getting something malicious past the gatekeepers is completely trivial. It's building the malicious stuff in the first place that's the hard part.
The way I look at it is that Apple's gatekeeper role is appropriately minimal on OS X and appropriately strict on iOS, and for my part I trust the twain will never meet because of exactly that "general purpose computer" difference, but you have added some thought-provoking perspective.