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I am using a Droid X, and have tried uploading a 27.28 MB file, taken on the phone, to youtube, via the youtube app and also via "share" option in Gallery. Neither has been successful. Most of the time I get the "Waiting for Wi-Fi" message, or "Waiting to retry xx minutes". I have tried it on Wi-Fi every time. At my home on WPA2, at a business customer's place using WEP, and neither work. I am going to try at my work which is unencrypted and see if I get better results.
I just wanted to say I get the same message on my Samsung Galaxy S with "Android 2.2.1" (hybrid).
Typically Picasa works, but Panoramio use to, but any more I just get that Waiting to retry.. I just uploaded 6 photos fine to Picasa, but then it hit one that displayed that message. I clicked it and hit "retry" and it went maybe another 1 or 2 percent, and then the same message. I canceled that upload, and the next 2 pictures went fine, and then bang.. the 3rd one spit that message out again. It's extremely annoying. I'm on a basically unused WiFi signal connected to a pretty fast cable connection. A 1.48M picture just did that, but a 1.50M and 1.58M picture after it worked fine.