What does a 'dotted-line' cloud icon in the iCloud file browser represent?
A dotted-lined iCloud icon means that it is waiting to be uploaded (or it is currently uploading). Although this KB article applies to iTunes Match, it might help you understand this icon better: http://support.apple.com/kb/TS4124

As for Byword's syncing issues, if it is not finished uploading, it won't be accessible by your iPhone. Are the subsequent documents also plain-text? This Byword support FAQ says that Byword's iOS app currently does not support RTF files (rich-text).