itunes 12.2.2.25 does not manage audiobooks properly

I have been ripping audiobooks from CDs for years and for whatever reason, iTunes 12 does not work predictably or dependably. My routine is a. rip the CD after joining the tracks so that there is only one track per CD; b. convert the file type from music to audiobook; c. create smart playlist with two rules (album contains: and 0 plays). I then sync the playlist to my phone. Several issues now exist. First, after selecting the playlist either as Audiobooks or "Include Audiobooks from Playlists" or both, the book will usually sync over to the phone. However, sometimes not all tracks come across. This is completely unpredictable.

The other thing that happens which annoys me is that even after I finish a book and trash the files, there are orphaned aliases in the itunes library which do not disappear. I typically delete the playlist, then delete the files from within itunes. Sometimes it is necessary to go to the Finder to make the files go away. But the alias remains. Anyone have any ideas on how to solve these? Thanks.