hey next_tech,
it seems to me like you should add the keylistenner to the JTextBox and not the JList, since the Enter key is suposed to add something to the list, it wouldn't make much sense to add something that is already there, or am I missing something?
Some source code would definitly help clear things up about your keylistenner question. But my advice at the moment would be "Make sure the listenner is correctly added to the JTextBox component".
As for file writing there are many tutorials easily found through google, such as this one which comes out first. I don't think you would NEED to serialize the JList, but then again telling us what you are storing in it would help!
if it's just a bunch of strings then to keep it simple i'd leave the JList as is and simply write all the items on seperate lines on the text file, and load each line to an item on launch.