I don't know how much progress you've made on the scripts, but I threw together a little mod to demonstrate that it's possible. The mod extends the built-in WICommentNaked quest.
The mod is not intended for general gameplay, hence the annoying messagebox on startup.
FNIS 4.0 and SKSE are required, manual installation, etc etc
edit: reuploaded the mod with some bugfixes. Also note that the mod will not respond to the OnEquippedObject event without a clean save.
CoverDemo.7z