Does this sound do-able?
Absolutely.
What software would be easy for a programming newbie?
Ummm. There don't seem to be any. Every language trips up any number of users. Personally, I like C# for GUI development, and it's ability to interface with the Arduino, via the serial port. The only difficulty is that the GUI runs in one thread, and serial communication takes place in another thread, so you need to code in the GUI to allow the serial thread to update the GUI.
I have a sample C# app that I could share. PM me with an e-mail address if interested.