I’m having this exact same issue. Same conditions. Uploading from the web admin interface works flawlessly, and uploading via XMLRPC posts the file properly (even sets the permissions I’m expecting), but I’m using Live Writer, and it’s halting the post publishing because of this error.
The only thing obvious is the following error in the log file for Live Writer:
WordPress database error Out of range value adjusted for column ‘post_parent’ at row 1 for query INSERT INTO wp_posts
(post_author
,post_date
,post_date_gmt
,post_content
,post_content_filtered
,post_title
,post_excerpt
,post_status
,post_type
,comment_status
,ping_status
,post_password
,post_name
,to_ping
,pinged
,post_modified
,post_modified_gmt
,post_parent
,menu_order
,post_mime_type
,guid
) VALUES (‘1′,’2009-07-08 12:16:30′,’2009-07-08 17:16:30′,”,”,’proshopteam.jpg’,”,’inherit’,’attachment’,’closed’,’closed’,”,’proshopteam-jpg’,”,”,’2009-07-08 12:16:30′,’2009-07-08 17:16:30′,’-1′,’0′,’image/jpeg’,’https://localhost/wordpress/wp-content/uploads/proshopteam.jpg’) made by wp_xmlrpc_server->wp_xmlrpc_server, IXR_Server->IXR_Server, IXR_Server->serve, IXR_Server->call, wp_xmlrpc_server->mw_newMediaObject, wp_insert_attachment”,””