How to animate a human written stroke using Swift/iOS?

You want to look at CGPathApply (this is the short answer to your more refined question). You supply it with a function and it will call that function for each element (these will be lines and arc and closes) of the path. You can use that to reconstruct each closed item, and stash them into a list. Then you can figure out which direction each item is drawn in (I think this could actually be the hardest part) and rather then using strokeStart/strokeEnd one each subpath draw it in a layer with a mask and move the mask across the layer.

A couple of concepts in the Apple CAShapeLayer (strokeStart and strokeEnd) really don't seem to operate as expected when animated.

But surely animating the strokeEnd is exactly what you want to do. Use multiple CAShapeLayers over top of one another, each one representing one stroke of the pen to form the desired character shape.

Progress Report

This answer is posted to emphasize the significant progress being made on solving this question. With so much detail added to the question, I just wanted to clarify the progress on the solution and ultimately (when achieved), the definitive answer. Although I did select an answer that was helpful, please consider this post for the complete solution.

Approach # 1

Use existing UIBezierPath information to identify segments of the path (and ultimately) make use of those segments (and their coordinates) to stroke each subpath (according to available language rules).

(Current Thinking)

Erica Sadun is producing a SwiftSlowly repo on Github that supplies many functions on paths, including what appears to be a promising library on Segments (of a UIBezierPath), Line Intersections and many functions to act on these items. I have not had the time to review completely but I can envision that one might deconstruct a given path into segments based on the known stroke types. Once all stroke types are known for a given path, one might then evaluate the relative path coordinates to assign stroke-order. After that simply animate the strokes (a subclass of UIBezierPath) according to their stroke order.

Approach # 2

Use a stroke-based font instead of an outline-based font.

(Current Thinking)

I have found a sample of a stroke-based font and been able to animate the stroke. These fonts come with a built-in stroke order. I do not have access to a completed stroke-based font that also supports Chinese but encourage anyone with knowledge of such a font to reply in comments.

I have made a recommendation to Apple that they supply stroke-based fonts in future releases. The Swift Playground notes and the files (with sample stroke fonts) are included in the question above. Please comment or post an answer if you have something constructive to add to this solution.

Stroke Order Rules

See the stroke order rules as described on the Clear Chinese website.