You are right, and the gap between what the system provides and what people actually need after a long sentence is significant.
Twenty-six years inside means he came out into a world that looks almost nothing like the one he left. Technology alone is overwhelming for someone reintegrating after that length of time. Smartphones, social media, online banking, digital job applications, and the general pace of modern life are not intuitive for someone who has been cut off from all of it for more than two decades. Add to that the psychological weight of institutionalization, the deeply ingrained habits of survival inside that do not serve a person on the outside, and the reentry challenge becomes clear.
The best things you can do practically are to be patient, be consistent, and help him navigate the specific obstacles as they come up rather than trying to address everything at once. Small wins matter. Learning to use a smartphone, opening a bank account, getting an ID, these are not trivial steps for someone in his position and each one deserves acknowledgment.
On employment, 70 Million Jobs is a resource specifically built for formerly incarcerated people and does meaningful work connecting them with employers who will actually hire. That is worth looking into given how many employers still screen out applicants with records.
Counseling and mental health support for long-term former inmates is genuinely underserved. Community mental health centers, reentry organizations, and some nonprofit legal aid groups offer services at low or no cost. Searching for reentry support services in your area is a starting point, and his parole or probation officer may also be able to connect him with resources tied to his supervision.
You being in his corner already puts him ahead of where a lot of people in his situation start.