Can you explain the differences between the following sentences?
They're puns. 

1: Winter: wear as much as possible, summer: wear as little as possible.
多少 means "how much", but could be read as 多+x "how very x", with x here being 少 （little).
2: 看不上 is ambiguous. She won't give anybody a thought. or Nobody gives her a thought.
3: "... then you just keep waiting." vs. "... then you can wait for your punishment."
4: 喜欢一个人 can mean "to like a person", can also mean "to like to be alone" (a verb like 生活 is implied, 一个人 is an adverb here).
5: 喜欢上 can be read as "started to like" vs. "would like to fuck" with 上 being read differently.
6: 睡过了: "he overslept" vs. "has slept (with her) before".