Thanks for all the tips.
I first approached this with intent to have fewer LONGER total clips per timeline, but ultimately all clips still residing on the same timeline. I strayed away from this early on as I didn't like how the chapters were clinging to nearest GOP, as I understood it, and my solution was to just add each clip separately, since the beginning of each clip serves as its own chapter marker. And here I am.
My other concern with multiple timelines is that I don't quite understand how to utilize chapter playlists across multiple timelines. For example, these movies span the years of 1992-2006, all home movies and such. I want a chapter playlist that is just ALL the Christmas home movies, another that is all the kids birthdays, halloweens, etc., and so having all clips on one timeline seemed like the easiest way to go.
There ARE more than 99 clips, 103 to be exact, but there are only 96 chapters. I dunno if that could be grossly affecting things or not.
I'm also realizing in this very moment the existence of "Playlists" as opposed to the "Chapter Playlists" I've been using this whole time, and how this may further enhance what I've got going on.
I'll continue to update as I make progress, and I appreciate the responses you've given so far.
PS. I've got a second project practically built, about ready to try and run "build" and see how it goes. It took about a half hour to put all the clips back in order, most have a date in the file name from when they happened chronologically and its mostly drag and drop, so I'm not opposed to really just starting completely over if it means making my life easier in the end.