I watched the first episode (which can be found here on youtube), and I found it amusing. I like how they're showing a balanced view - you don't just get the cool and bizarre, but also the seedier, darker side of Japan that most things like this would just gloss over or ignore. That, and it's amusing watching a self-proclaimed stuck-up princess forced to do all sorts of uncouth tasks.
“Kelly Osbourne loves shopping in Japan, but will her working holiday leave her dying to stay or longing to leave? Her first raft of jobs include managing a Tokyo Love Hotel, training with the Samurai and waitressing in a very strange cafe.”