The problem with you upload was the server timed out before the pictures completed.  We have verified that in the log file.  How large were the original pictures?

• The timeout could be cause by connection problems with you ISP.
• It could be caused by general Internet traffic.
• It could be caused by very large picture files. 
• It could be caused by network traffic at our server farm.

We have increased the connection time out limit.  We will see what that does.  If we increase it too much it could cause server slow downs on our end.

To answer your last question, the post has to be created first so that the pictures can be attached to it.  You can't upload pictures to a post that does not exist yet.  That is the short and dirty answer.  It would require very major code rewrites to change that.  The new file upload allowing pictures to be rotated took much more new code that we expected.