Okay, here's where things start to look like I might be having two problems simultaneously....!
The thing is, as this was all starting, I was *pretty* sure that I was having SUCCESSFUL workbench uploads (i.e. uploads where I DIDN'T get the error message) but where my uploads still never appeared on workbench. But by the time I started paying close attention to what was happening, I was getting the error messages every time, and that's all that's happened since (for workbench), so that's what I posted about. (I still can't remember with 100% certainty whether these "no error but no upload either" attempts happened, or if I'm misremembering.)
But, now that you mention it:
if I am uploading to SANDBOX:
1. I sometimes get the error message
2. but I always get the confirmation email (I'm pretty sure)
3. and the link works perfectly in iAd Tester
BUT!
if I am uploading to WORKBENCH:
1. I ALWAYS get the error message
2. I NEVER get a confirmation email
3. it NEVER shows up in Workbench
So, my experience with Sandbox sounds like your experience, but my experience with Workbench might be something different... (I wish I could remember clearly whether I'm remembering correctly about initially having successful uploads that never appeared, argh.)
Also, I might as well ask -- is there a simpler way to see the list of ads uploaded to my workbench, other than to try to assign a creative to a new ad in a campaign? I'm worried I might just have something configured wrong that's keeping me from seeing certain uploads... (Also, is there any way to see a list of what I've uploaded to Sandbox?)
By the way, I did the thing you mentioned about uploading to sandbox and then contacting the Workbench team, but I still haven't heard back from them...
Thanks again for your help on this.