The $99/year thing is not
terrible. I remember saving money from my paper route to buy tools/lib licenses to some specialized things I really wanted.
Selling your parents on a single $99 purchase is a lot easier than trying to sell a $5 purchase every week. 'Tis just the way it is.
jarin below mentions he wouldn't hesitate buying his kid Xcode for $5... that only works if the parent is in the field also. How many, say, accountants or lawyers would buy their precocious coder-child a bunch of tools or understand the importance of it?