Hey! Thanks for the bug report and for the VOD! I'll definitely be watching the whole thing.
As for the bug itself, I guess this is sort of the flip side of a bug I already knew about. Chako's sleep sequence is based around whether or not you have to lipstick, so: (1) If you already have the lipstick, then you can never get the item which was placed there, (2) If you don't have the lipstick, then you can collect the item which was placed there an infinite amount of times.
I'll try to have this fixed fairly soon, although I'm a little busy these days so I can't promise it will be immediately.