ITunes having trouble syncing to my iPad?

Question

Okay I have been having so many problems since the newest iTunes update. I was trying to buy a song on my iTunes for the Mac, and when I went to sync my iPad it removed 39 songs from my iPad. I tried to sync yet again to get these songs back and it said 39 songs could not be copied onto your iPad because they have not been found. This puzzled me because they had always worked before, and suddenly they stopped working. Half of these songs were songs that I purchased on iTunes so that's what's confusing me the most. The other songs are songs from a CD that I downloaded. Is iTunes really being that cheap now that you have to buy every single song from them and can't even burn CDs on iTunes anymore? It's pathetic. I am getting so frustrated with Apple. It seems like with every iTunes update there have been more problems.
I have tried manually syncing these songs separate from my library by artist and album, and nothing seems to work. I have tried just about everything at this point. I am so upset as some of these songs that aren't dowloading are some of my favorite songs. If anyone knows how I can fix this I would greatly appreciate it! Thank you

Answer 1

Your second troubleshooting step should always be updating iTunes. To make sure your up to date you do:
MAC>click to on iTunes to make it the active window click iTunes>Check for updates...
WINDOWS>click Help>Check for updates...
If your iTunes is up to date restart both devices the iPad and the computer your transferring music from.
Make sure your computer is signed in to your appleID and that you purchases are all downloaded on you system by:
Clicking Store>Check for available downloads...
This ensures that all purchased content has been recieved from your iTunes Store as the content your trying to sync MUST be present on the system your transferring from.
Click Edit>Preferences
Click "Devices" at the top right
Put a checkmark in the box beside "Prevent iPods, iPhones and iPads from syncing automatically"
Plug in  your iPad
Click the name of your iPad to display the Device Summary page
Click on Music at the top
Put a check in sync music manually
All items on your computer available to sync will be displayed select the items your wish to transfer and click sync in the bottom right
This should manually sync the content your looking for.
You can then turn automatic sync back on by:
Click Edit>Preferences
Click "Devices" at the top right
Remove the checkmark in the box beside "Prevent iPods, iPhones and iPads from syncing automatically"
This can be an issue generally when iTunes doesn't have the content, your trying to sync to much content.
Remember that if your trying to sync a playlist it requires all the music to be present in it's orignal state to process.