Usually, a week or two depending on their orientation schedule

They should be able to deposit the check into their Inmate Account. However, you should call the facility and ask to speak with the inmate's case manager or counselor before sending anything. They will give you the proper instructions on how to proceed. Be sure to take notes from your call to them

The typical calculation is 85% of your sentence is what you'll serve. That equates to 15.3 months, with 4 months already served, there is 11.3 months remaining

Inmates can use their money in their Inmate Account to buy commissary, add talk time to their phone, send an email and even send money home to family members.

Generally older inmates are left alone unless they have a big mouth. If your female friend is on her second bid (for murder?!?), she knows the score better than we could advise. She'll be a real gangster in there

Halfway houses are allowing their residents to own cell phones now

Money on the books at the county jail is not transferrable in traditional ways. The inmate has to request a check for the remaining balance to be sent to their home address. Adding money to an inmate account in a State Prison starts anew, with new funds. If the inmate gets moved within the State system, the funds will transfer from facility to facility. 

Send him a postcard, that is the easiest, fastest, and least expensive

He will be wearing clothes that fit him when he is released. 

There are specific medical procedures available to your inmate that he can follow to get it taken care of. There are forms that he should get from his counselor or case manager to get the process started and submitted into the system. This is a very slow process so patience will be required. You, as an outsider can do very little but call the facility and try to find a sympathetic ear to inch along the approval process.