I realized when I started running into stability problems with the debugger that I am actually using an older version of OpenOCD in the tutorial below (build 717 which is quite old by now). I was pointing to the wrong folder, since I had two different versions installed. My bad.
I am currently in the process of trying to get everything to work with the latest official release of OpenOCD, and once I can figure out how to properly configure Eclipse I'll post the configuration files here, and explain any particular hoops I had to jump through to get the debugging working. I'll try to make a full post on configuring OpenOCD again, just to avoid any confusion and having to switch between the two articles trying to figure out what's different, etc.