Animating a logo outline

This is not a super special case, you're just going about it the wrong way by trying to do everything directly on the layer, no offense. It simply boils down to the techniques used in the millions of "logo reveal", "handwriting" or "hoolidander/ growing swirlies" tutorials that were hip 15 years ago - you use track mattes and create the "sloppy" stuff on a different layer. In case of a compound path this could be as trivial as creating a blend with just one step to get the centered "spine" in Illustrator and importing/ copy & pasting it over to AE on a solid layer atop the footage you are trying to reveal, apply an animated Stroke effect and assign the solid as a track matte for the layer underneath. This works 90 percent of the time without any further adjustments and when it doesn't, most of the time you're simply going to need some additional masking or tweaking the stroke path to avoid kinks e.g. where sharp corners self-intersect. Likewise, you may simply need multiple masks, strokes and so on or even use multiple layer duplicates that are mutually masked for multiple letters and sub-strokes. Again, all tried & true techniques that have existed forever. I'm sure you can find those tutorials from way back then or contemporary ones with similar techniques. YouTube usually gets flooded with such stuff when something becomes hip. Even Andrew Kramer did one on it over at VideoCoPilot.net. I suggest you look them up and come back if you have specific questions.

Mylenium