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Follow the quest tree for Chloe. Look for other new options that appear for her and try them. 

It was under the lost and found in the laundry room if you are talking about the cross key

You have to check if there is a new option and do it a few times to get a new option unlocked. Check the quest tree and see if there is a mission you didn't do.

The maid requires books as gifts to help increase her hearts to be able to do more stuff.

Stealth is needed to unlock certain scenes and interactions. If your stealth is low you probably missed them and will miss the later interactions in the next patch. Max stealth by licking dana's breast during the night when she is asleep.

Some sexual scenes and interactions can only be done with higher stealth. If your stealth is low and you want to see scenes that require stealth you have to level it up. There are a few awesome scenes and sexual interactions you probably missed and are going to miss in later patches due to low stealth. Keep licking Dana's breast during the night when she is asleep to max it.