Thanks for the tip on the 'from ... import' statement, EnTerr. It would seem very appropriate in that case. I remember coming across it, but didn't look into it further as I'd already got my basic imports working.
I've been looking into doing a GUI debugger wrapper. It has a lot more potential than my Python attempt (in addition to the command history and logging: multiple tabs for different Rokus/ports, discovering the Rokus on the network, a drop-down menu listing all the Roku ports, a clear-screen key, ... -- probably stuff that Eclipse already has, if I hadn't given up on trying to get it working).
I've never thought that Roku needed a full-blown IDE, although I haven't personally worked on anything that I thought would benefit from that. A "Roku IDE" would probably have to be platform-independent, which is what Eclipse claims to be -- if you can get it to work. If I was really interested in such a project, I'd probably write a Visual Studio extension, since that's what I've been using for most of my development recently.