So after trying to resolve this issue for a better part of the day...Tried the following:
1. Restoring iPhone from backup
Result: Did not work
2. Deleting all playlists from iPhone and re-syncing
Result: Did not work
3. Re-Authorizating my Mac
Result: Did not work
4. Made sure all my settings were correct to manage my own playlists
5. Delete all but 1 of my iPhone back up via iTunes, and renamed that one file and placed it in a secondary location, sync'd and created a new backup
Result: Did not work.
6. Created new playlists via Duplicate option in iTunes
Result: Did not work
7. Reinstalled iTunes
Result: Did not work
8. Recovered backup of iPhone from a week ago via Time Machine
Result: Did not work
9. Deleted all voice memos
Result: did not work
I did read on a post and saw some success with this:
10. Unchecked Sync & deleted all my music off, unplug, and re-sync and check back Sync for music.
Result #1: This eventually brought back my playlists onto my device, however, (This is the most important) playlists were not updating from the changes I would make to them, or when I try to import a new playlist to my device.
Result #2: I would go into iTunes and when i select my device and select "On my Phone" I could see the playlists that sync'd correctly and the ones that didn't (The ones that didn't sync were grayed out)
Result #3: Syncing 2K+ songs this way is way too difficult, if I wanted to make changes to my playlists over and over again.
Result #4: WAS NOT going to accept this as the fix, as it was the only work around.
Attempt #11 finally resolve the issue for me.
I decided to recreate my iTunes Libary & Playlist.
Follow the instructions in the Knowledge article below and after you plug your device back into your Mac, you will need to allow iTunes to select your mac to conduct your back ups. After this, you'll be able to make modifications to your playlist and it'll sync like before within iTunes
http://support.apple.com/kb/ht1451
Cheers,