From testing if you have the following conditions statuses/update will fail
- 140 characters
- media_ids
- attachment_url
It looks like if you use attachment_url and media_ids in conjunction with each other, the character count needs to include the length of the original status link.
Is this expected behaviour or a bug as the display_range does include the link to the quoted_status, omits the media url but DOES include both the quoted_status object and the media entities in the tweet response