Would it be correct to say that it is harder for a weak electrolyte to dissociate in a solution than it is for a stronger electrolyte to dissociate? If a weak electrolyte can't dissociate completely it wouldn't be able to form an equilibrium reaction right?

yes

Second question: No Equilibrium does not depend on complete dissociation. At equilibrium, the rate of dissociation is equal to the rate of reassociation.