Solution / Lessons Learned:
When populating a multi-column listbox, it is much better to set the RowSourceType = "Table/Query" than it is to use a "Value List". I was having issues with populating the multi-column listbox with various string literals and other pieces of data. I was having issues with escape characters, or characters in the string literal would act as delimiting characters. Adding escape characters worked to some extent, but required much more manipulation and code. I actually hit a point where my wrap/escape characters would not properly delimit my addition string. All my columns were shifted over at these delimiting characters.
I changed my RowSourceType to "Table/Query" per the advice of @June7 and this has solved my problem!