From everything i have read and discussed, and in no way am i saying i am knowledgeable, but i have thoughts only........ i don't think that you can expect anyone after spending more than 20 years inside a dog box to come out and not be effected for life. Be it the mattress too soft, so many choices that lead to a feeling of being overwhelmed and confused. Wanting to always be in a position their back is not exposed. Technology and traffic, everything moving too fast. Loud noises can effect those that have spent a great deal of time in solitary, and then you have social anxiety disorders. Some do not even understand privacy. Then you have all the other small things like how fast they will eat, and the way in which they eat. So many little things that you wouldn't even think of.
Post Incarceration Syndrome, PICS is something you may want to read up on. I honestly believe you need a plan of attack for the time your loved one is released, if not professional help, then a great deal of patience and communication with both eye's open and an understanding and patient heart.
I am sure they can be productive members in the free world, but not without their own personal scars from their life experiences behind the wire.

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The last of all freedoms is the ability to choose one's attitude in a given set of circumstances.
G. W. Allport.