Uploading songs from PC to iCloud

I am having numerous issues:

1) I want to sync only the checked songs - like you used to be able to do - and it will not transfer only those songs to my iPhone (4s).

2) The large majority of my songs will not transfer to iCloud or Match - I get the cloud with the exclamation point in it, indicating there is an error in the transfer.

How do I transfer only the songs I want to my other devices?

How do I fix the errors so ALL of my songs are transferred to the cloud, rather than just a small percentage of them.

I am getting very frustrated! The songs I want on my devices are not there, even though only the ones I want are checked in my iTunes library on my PC.

HELP!