I was having this same issue yesterday, and as explained by jrodman when you use the wildcard, it then "changes" how it's looking at that path and is looking for the filename to end at "Logs". Not exactly how he explained it, but close.
Modify your monitor stanza, adding "\*" to the end and it should begin working. You can query the REST api to find out why it is or isn't picking up files at the following url:
https:// :8089/services/admin/inputstatus/TailingProcessor%3AFileStatus
You'll need to have changed the default admin password unless you're connecting via localhost. If you look at this url now, it should list the files under your Logs directory, but complain that they don't match the whitelist of: C:\Program Files (x86)\DirectoryName.*\Logs$
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