If you have a video cam, it might help to post a short flick of your entire technique in the '
Videos of espresso extractions' thread. I agree with Jim - I've never seen a coffee stale enough that a good grinder couldn't grind fine enough to choke a machine.
When I was starting out, I kept reading that espresso requires a 'fine' grind. Well, I didn't know if that meant it should feel like sugar granules or flour dust. So I tried many different things and after much wasted coffee and time and a lot of frustration, I've come to the conclusion that it's somewhere in between both but closer to the latter. What I may interpret as 'fine' may be understood as much coarser to someone else, so using words like fine or coarse don't really help when trying to talk about this stuff over internet forums. So when you say you set your grinder to fine, it's still probably not fine enough. Don't be scared to adjust it finer and finer until you hear a horrible screech - it's unmistakable, and it's your burrs eating each other, and it's really bad.
What you could try is going to your local coffee shop and asking them to grind you some coffee. It's going to go stale really quickly, but bring it home as fast as you can and try that. Compare the fineness to what you are producing at home. It's always helpful to have some sort of real world reference.
Forgot to mention something. It's interesting to note that as learning home baristas, we individually tend to question both our technique and our equipment. This inevitably leads to time spent on improved technique and money spent on better equipment. When it comes down to the individual, at least in my case, one tends to try to blame the equipment for repeated less-than-stellar results. Conversely, when questions are asked here on the forums, everyone else seems to think there is a problem with your technique. And it just so happens that everyone else is, more often than not, correct. There are of course exceptions, but I've always found it interesting that for most, it's a lot harder to believe that technique is at fault rather than the tools when it comes to self criticism, but the opposite is true when you are criticizing others. Just a thought.