I am having sort of the same problem still… I don’t see any error numbers and the old fashioned upload link is not anywhere to be found. I am new to WordPress. I get the IO Error with the message to try again later. I am using Firefox and have IE Tabs Extension for Firefox installed. When, and only when I have switched over to the IE Engine can I upload images. I have found that just accepting the security certificate in the IE Engine and then switching back to the Firefox Engine I can upload images, (using the Firefox Engine) until I restart Firefox. So, is this a problem with Firefox, WordPress, or my server?
P.S.
I have read through and tried all of the solutions posted here and none of them worked for me. Also, I do use the DNS service offered by dyndns.org because I have a dynamic IP if that is relevant.
Thanks in advance…