iTunes Playlists Not Syncing Correctly...Again!

So, since the latest update to iTunes and the release of iOS 9.1, iTunes is, once again, not syncing my playlists correctly. I though they had this fixed in the previous version, but, lo and behold, syncing issues are back again.

BTW, I am syncing with an iPhone 5 and with a Windows PC.

After I purchase a new song from iTunes and try to add it to a playlist, then sync my iPhone, that new song will not show up in that playlist on my iPhone. Neither will it show up even in the Recently Added iPhone native "smart playlist". However, it will show up as being added to the phone if I search for it.

Strangely, ifI add songs previously ripped from CDs to playlist, they add just fine.

I haven't tried adding songs purchased from iTunes before this latest update.

In any case, can anyone help me out here?

Usually when I un-sync all my music and re-sync it again, that takes care of the problem, but only temporarily. The next time I try to purchase a new song and add it to a playlist, the same thing happens, so I have to un-sync/re-sync again.

Does anyone have a quicker and/or more permanent fix for this?

Has anyone else even had this issue? If so, has anyone reported it to Apple? If so, what has been their response?

Thanks.