*** UPDATE ***
Well, one of those funny things happened. I came to realize that my understanding of expandPath() is wrong. After having used it in a manner that was not as the function intended (but the result worked), I have now realized that this fluke needs to be resolved to a point where I can understand how expandPath(), directory/fileExists() and CFC dot notation works alongside CF mapping.
I've been at this problem for about 4 hours now and nothing has made any sense. The documentation provided by Adobe raises more and more questions and all the local testing I've been doing (where I'm ADAMANT a file exists and am being told it does not, and when I do something that should not exist, I'm being told I pathed to it properly).
In these situations, it's always best to leave the problem alone and hit it again tomorrow from a fresh perspective, so I'm admitting a defeat with an asterisk for the time being, but I'll get at this again tomorrow.