ITunes music sync problem: "drag & drop" works; "Sync Music" doesn't?

I've been trying to sync a few new playlists of music to my iPhone 3GS with frustrating results.
I'm hoping someone can explain to me what I may be doing wrong.
In the past when I wanted to add new music to my iPhone I would use what I refer to as the "Sync Music" or Music tab method.  I would rip the CD, create a new playlist for the album, plug in my iPhone, select it under the Devices list in iTunes then click on the Music tab up at the top of iTunes (I have "Sync Music" checked and "Selected playlists, artists, albums, and genres" checked.  I would scroll down through the list of playlists, find the new playlist I created and check the box next to it and sync my phone to add the new music.
This has worked flawlessly for years.  Until now.
The last three albums I have tried to add this way will not sync to my 3GS.  The music will play perfectly on my MacBook in iTunes.  I ripped the music the same way, created the playlists the same way, and I can even get as far as the list of playlists under the "Sync Music" check box in the Music tab.  I can see the new playlists in this list, I check the boxes indicating I want to sync them to my phone, but when I click Apply and then Sync, the music never shows up on my iPhone.
I keep every new album I import in it's own playlist, so being able to select which playlists I want to sync to my phone is definitely the method I would prefer to use, but since it wasn't working I tried checking the box next to "Manually manage music and videos" on the Summary tab.  This of course disables the Music tab and unchecks the box next to "Sync Music".
I'm not too familiar with using this method to manage my music library, so maybe someone can show me a better way to do this, but with the "Manually manage music and videos" box checked the only way I know to add music to my iPhone is to drag a playlist one at a time from my iTunes library to my phone in the devices list.
This is where I get confused.  For some reason the new ablums I ripped, which I was unable to sync the way I am used to ("Sync Music" check box/Music tab method), can be dragged and dropped onto my phone and they are copied to the phone without a problem.
WHY!?
Why, am I able to sync these ablums using this tedious and clunky drag and drop method and yet I'm unable to copy them to my iPhone using my prefered "Sync Music" checkbox method?
If you have any idea why I'm experiencing these problems or if you have experienced a similar problem please let me know.
Thank you.

This problem started last year when ios 8 was released. I think apple is trying to force users to buy music on iTunes store and that's why it's impossible to sync other music and also that's the reason why they haven't solved this serious problem. That's really disappoints me and i'm angry with apple because i have like 10 gb of music in mp3 and i can't sync music from iTunes to my iPhone.

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