http://www.theolympian.com/2010/04/18/1209941/kid-writes-iph...
And you don't need a relatively new Mac, just a Core 2 Duo Intel or newer (I have a 3 year old MBP and can sign/develop for iOS 6 beta seed 1).
And it requires absolutely zero technical knowledge: You just drag and drop an .ipa file, and sync with iTunes.
Xcode is free.
So, only your first argument ($99/year, for 100 devices) is actually correct.
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I hate being forced to defend Apple in a case that I don't agree with what they did, but your very poor criticism made me to correct you. I'm sure you understand that it's nothing personal, and doesn't mean I agree with what Apple did.
Only if we allow you blowing off the "need a Mac" requirement to equal zero dollars...
It's kinda a decent sized hole in your argument.
However if I were to play smart I'd say I didn't have any argument and was just refuting my parent's :)