It looks like Kenny 's answer above points to the right solution in the referenced question, but may have taken away the wrong concept. The UIView class reference definitely suggests a system for making sizeToFit relevant to your custom views.
Override sizeThatFits, not sizeToFit
Your custom UIViews needs to override sizeThatFits to return "a new size that fits the receiver's subviews", however you wish to calculate this. You could even use the math from another answer to determine your new size (but without recreating the built-in sizeToFit system).
After sizeThatFits returns numbers relevant to its state, calls to sizeToFit on your custom views will start causing the expected resizes.
How sizeThatFits works
Without an override, sizeThatFits simply returns the passed-in size parameter (defaulted to self.bounds.size for calls from sizeToFit. While I only have a couple sources on the issue, it appears that the passed-in size is not to be seen
answered 2012-12-11T21:17:58.810