Who needs more sleep? This boy... Therefore the subject is altered "Етому Мальчику" If not... no subject is defined and it could be... Sleep needs more boy.
This is the case system as I understand it... but I am also just grasping this idea so I could be incorrect.
Abbreviating "have" like this (should've = should have) is only done when "have" is used as an auxiliary verb in a compound verb, such as "should have gone" or "should've gone". Even then, it's very colloquial English, and Duo shouldn't accept it even when correctly used.