Yes, it should always be hyphenated.
Yes, back-to-school is hyphenated when used as an adjective phrase before a noun, such as "back-to-school shopping."
"Mid back" is typically hyphenated when used as an adjective to describe the area between the upper and lower back.
no it is not hyphenated. It isn't because you have added a prefix ( a bit that changes the meaning and goes at the front, if it is at the back, it is a suffix.)
It is not hyphenated.
Motorcycle is not hyphenated
No it's not hyphenated.
words are only hyphenated when they have a separate meaning when separated than they do when hyphenated
Yes it should be hyphenated.
No, "hardworking" is not hyphenated.
It can be. Some words can be seen both hyphenated and non-hyphenated.
No. Well above is not hyphenated.
peace of mind is not hyphenated.