A new generation of children with hearing impairment (HI) has emerged due to the introduction of universal neonatal hearing screening, medical–surgical/technical and educational advances. Aim: Investigation of long-term development of vocabulary and social well-being of children with HI, including children with HI and additional disability. Method and Material: The project design was prospective, longitudinal, and comparative. Level of receptive vocabulary was compared to children with normal hearing, type of hearing technology, gender, additional disability, diagnosis of HI, level of social well-being, and start age for use of hearing technology. A total of 231 children participated. Intervention included early start of hearing technology and three years of auditory–verbal therapy (AVT) at the preschool level, followed by 3 years of AV guidance at the school level. Results: Children with HI scored within the norm for receptive vocabulary but were outperformed by the control group. Children with HI and a diagnosed additional disability scored lower than children without additional disability, in terms of parental assessments of social well-being. Children with additional disabilities showed positive progression in terms of receptive vocabulary development. Conclusions: New generations with HI possess the potential to succeed academically in accordance with individual abilities and become active participants in the working market.