Why won't my iPhone 5S sync with my computer?

I have the grey-dotted circle issue that has been addressed in other discussions before (even though I did not get a straight answer from there). Whenever the iPhone 5S (which is running iOS 8) is plugged in, it says that X amount of songs are greyed out in the 'On my phone' page. Not quite sure how to fix that.
However, whenever I try to 'apply' changes, and sync to the computer rather than iCloud (which by the way is ridiculously slow as well---icloud sync), it will go to 'step 4' or 'step 6' where it's applying changes, or finishing up, and just stays there. It freezes.
This all happened when we tried to sync a new playlist to the device. It said in the play list that there were 250+ songs, whereas only 56 transferred to the phone....(this is where the grey dotted circles in the 'on my phone' screen comes in) Some of the music in our library is older and has been transferred from computer to computer over the years. I've tried de-authorizing the computer then reauthorizing since it said we couldn't authorize more than 5 devices to the same library but that was to no-avail.
We have upgraded our iMac to Mavericks, iPhone to iOS8 and iTunes to 11.4. We rebooted everything yet we are still having issues.
Some help would be appreciated. This device will be used as a music source for a marathon within the next week and we'd like to get the device up and running for the runner who will be in the marathon.
Thank you in advance.

Launch the Console application in any of the following ways:
☞ Enter the first few letters of its name into a Spotlight search. Select it in the results (it should be at the top.)
☞ In the Finder, select Go ▹ Utilities from the menu bar, or press the key combination shift-command-U. The application is in the folder that opens.
☞ Open LaunchPad. Click Utilities, then Console in the icon grid.
The title of the Console window should be All Messages. If it isn't, select
SYSTEM LOG QUERIES ▹ All Messages
from the log list on the left. If you don't see that list, select
View ▹ Show Log List
from the menu bar at the top of the screen. Click the Clear Display icon in the toolbar. Then take one of the actions that you're having trouble with. Select any messages that appear in the Console window. Copy them to the Clipboard by pressing the key combination command-C. Paste into a reply to this message by pressing command-V.
The log contains a vast amount of information, almost all of which is irrelevant to solving any particular problem. When posting a log extract, be selective. A few dozen lines are almost always more than enough.
Please don't indiscriminately dump thousands of lines from the log into this discussion.
Please don't post screenshots of log messages—post the text.
Some private information, such as your name, may appear in the log. Anonymize before posting.

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