Why won't my downloaded apps transfer from my PC to my iPad?

My boss let me take over his old iPad. I don't now what generation it is. He said he's had the device for about 4-5 years now. I told him to erase everything and I thought he did. It was easy for me to get rid off all the apps he was using. But now I'm having a hard time with the device. Some of the apps I've downloaded from iTunes will not transfer on to the device. When I try to sync songs from my playlist at home a lot of the songs will not transfer over to the device. I am also having trouble of getting rid of some photos that my boss put on the device. And I am having trouble erasing all of my bosses saved dates on the calendar/planner so I can use it. Please help.

Sounds like you boss did not erase the iPad.
You should try to erase the device on your own in Settings>General>Reset>Erase all content and settings. If the device is running less than iOS 7, that is all that you need to do in order to erase it. If the device is running iOS 7, you will need your boss's Apple ID and password in order to erase the device or he will have to do it for you. This explains what he/you will need to do.
What to do before selling or giving away your iPhone, iPad, or iPod touch
You can check to see what iOS is on the device in Settings>General>About>Version.
After the iPad is properly erased, you can set it up again using a WiFi network - or iTunes on your computer. The setup assistant will guide you through all of the steps that you will need to go through in order to activate the iPad for your own use.

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