I'm a 2nd year university student, and I thought it would be a good idea to expand my abilities. I will be using python later this year to complete a gui for a  C program (using Tkinter), but I want to make a side project as well, and python seems like a great language to do it with. 
I want a project which has multiple levels for me to code, so it's definitely going to have a gui and command-line version, and then maybe some database stuff (since I would like to know more about SQL and other database tech). 
I thought I could make a music player. Start by just making a command line program which plays a music file, then expand it from there, probably using pygtk for the gui.
Considering I have no python experience, but I do have a strong background in C and Java, are there going to be any difficulties which will unexpectedly stop me? I have never made a music application before, and I am not sure whats involved in keeping a music library, for example.
Are there any other projects you might recommend, that can be completed in about an hour a night, for 3 months? (Or get a significant working program out of it, even if its not complete).
Thanks!
Writing a program will help you learn the language, but IMHO joining the development team of an open-source python project would help you learn even more, as reading high-quality code written by other developers will disclose to you features of the language that you would never discover alone.
So, my suggestion is to hunt for a smallish and high-quality python open source project, read its code, understand what it does and then start contributing. It might help to choose a project that you use or that you like.
A good side-project for learning python?