Hi there!
Very interesting project, I may be very well suited to complete this for you, or I may not, really that'll be decided in the next few sentences. I am not a Python programmer - if the Hard Mode option absolutely must be in Python, I'm afraid I'm not the Freelancer for you. However, nothing in your proposal suggests that an alternative method would not work correctly. Specifically, I work in C++ with wxWidgets, and have experience creating boot-to-software (or "kiosk") Raspberry Pi programs.
Assuming a non-python option is viable, allow me to elaborate a little. The easy mode is straightforward enough - tell me which operating system you'd want it for and I could have a binary to you within a day, easily. I listed my price for this as $40 as it indicated this was the prepaid amount. For the hard mode, obviously we would have to discuss further pricing/time considerations.
That said, the hard mode would also be relatively straightforward - I know of a very reliable method to boot a Raspberry Pi straight into the software, have a program gather GPIO data from the pi and use those inputs to play sounds and determine states - I've already done all of that in a previous project. The really hard bit of the hard mode, to my knowledge, would be hooking up the pi to the phone buttons. I'd love to go into more detail with you but I'm running out of characters on my proposal. Assuming a C++ application is okay, please do contact me and we can discuss it further.
Chris