For me jailbreak is out of the question. I have a fairly large website
www.iTeams.mobi that I created specifically for the iPhone and was hugely disappointed when I saw the phone didn't support a feature that I thought was a no brainer.
Many folks who use iTeams.mobi have iPhones but they have to upload their photos via a PC/Mac browser. For them jailbreaking is not a viable option.
I'm not keen on any kind of add in or seperate app to accomplish this functionality since I don't think people want to deal with that. But on the other hand I have waited close to a year now for Apple to add this feature and if it doesn't come this time then chances are it will never come.
-Al