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Subject: Sending mail inside
The sketch pad will probably need prior written approval from the prison - sending blank computer paper will be fine and YES he will be able to bring these possessions home with him.
Subject: Survive prison
This is a complex question best answered privately - the short public answer is it can be as bad as TV or a tame as a camp setting with white collar non-violent offenders. It really depends upon where he is sentenced to do his time. Other factors are the type of prison - whether its a state or federal facility, the length of the sentence, the crime and the sometimes the determining circumstances of the crime. But an inmate that...
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Subject: Visitation
YES, You can definitely get more visitation time being from out of state. The only thing that you need to do beforehand is to have your inmate fill out a "special visit" form and get the visit approved by the warden or whomever the person is a his facility that approves such things.
Subject: Offender phone calls
You will have to notify your inmate of the new number he is dialing out so it doesn't need a name attached. You will have to fund this number with the prison carrier separate from the long distance number you use now. The carriers won't transfer numbers, BUT this account will be at the LOCAL rate which should save you about 70% off what you are paying now. We will have your new number within a few hours.
Subject: Send books and magazines
[Amazon](http://www.amazon.com/b/ref=as_sl_pc_tf_lc?node=283155&tag=inmatecom-20&camp=15329&creative=394453&linkCode=ur1&adid=1NK4T3Z8XDKYJ0S12D53&&ref-refURL=https%3A%2F%2Fwww.inmateaid.com%2Fpages%2Fdetails%2Fsend-books-to-an-inmate-in-prison-or-jail) is one of the only companies that may deliver books to inmates. You have to enter the inmate's name, ID number and the correct address of the facility. You have to buy "new paperback books", the used books are sold by third party affiliates and those books will get rejected. There are no other tricks to it, other than staying away from the other book sellers on the Amazon site that sell used books.
Subject: Commissary
There are no current online services for Cuyahoga County Jail, they only accept money for an inmate "in person" - you can't even mail in a money order.  This is not a normal practice, usually Western Union is available for putting money on the books for inmates.
Subject: Commissary
Any money deposited in your commissary account that goes unused is returned to you upon release. 
Subject: Visitation
They do not release on the weekends. It will be up to the individual facility as to which day they choose to release him, Best guess would be Monday the 20th - but we suggest you call the facility and ask them what they intend to do.
Subject: Sending mail inside
You have registered as a user, but you need to register your inmate here, too for them to appear in our listing. If you do not have their number, give us the information and we will try to locate as much information as we can for you. Full name, DOB and state would help.  Once you have this set up in the system, when you use our letter writing service, we do all of the addressing to the prison with...
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Subject: General prison/jail questions
There is one that we can recommend called The Innocence Project of Texas - you can find them at www.ipoftexas.org.