The requirements seem a bit unclear to me, but I'll toss a couple of titles into the ring: The Inmates Are Running the Asylum (Alan Cooper) makes the case that

The requirements seem a bit unclear to me, but I'll toss a couple of titles into the ring: The Inmates Are Running the Asylum (Alan Cooper) makes the case that user interfaces can and should be easier to understand. I think in the years since this book was written, there has been much improvement in the UI world overall, but still worth thinking about. Expert C Programming (Deep C Secrets) (Peter van der Linden) goes into some fascinating technical (and historical) tidbits related to C.