I worked for the California state system, starting as a Correctional Officer and retiring as a Lieutenant in 2005. I now write for the PacoVilla blog which is concerned with what could broadly be called The Correctional System.
They didn't use to be, but some are now fussy about visible ink, especially if it something that even looks like it might be gang oriented. You might have to invest in some really good cover makeup or tattoo removal.
A white guy has a much easier time of it in prison, generally speaking, than would a black or a Hispanic, at least in the CA system. There is a lot of pressure for blacks to choose sides, and even more than that on Hispanics. As long as you hang out with white guys the others will leave you alone (mostly-probably) and the whites will not apply undue pressure to join gang activity (mostly-probably). If they believe you have money they might target you for "rent payment."
The law, and administrative rules, will vary from place to place. In California, and I suspect most states, the relationship would have to be reported both to the probation officer and to the officer's chain of command. It would be at best seriously frowned on and likely prohibited. A person on parole or probation is still under the jurisdiction of the department and is under constructive custody if not actual custody. Any personal relationship, especially a sexual one, could be considered to be coercive.
You can expect a certain amount of "hazing" and resistance. The inmates will normally want to see if they can push or fake you out. Normally on a first day you will be in the company of an experienced officer who will (hopefully) give you a feel for what is going on. You will, however, obviously be a newbie. Your uniform will be new, you will not know the language and you will probably seem a little unsure or hesitant. You will not even know where a lot of things are. Its not a big deal, and it is not generally speaking personal.
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First you might want to try to figure whether or not your brother is telling you the truth. I know it is hard to believe but prisoners often lie about being mistreated. Assuming for the sake of argument these allegations are true he needs to have his injuries documented if possible as quickly as possible after they occur and needs to contact whatever internal affairs operation they have where he is or if push comes to shove contact the feds. Assault Under Color Of Authority is a very serious crime and the state(s) and the feds do prosecute such things. You could make an initial contact on his behalf with these authorities, but he needs to be willing to go on the record at some point with these accusation to make anything stick.
I am unfamiliar with the laws and rules in Florida. If I were to GUESS the answer is no, but you can count on them looking very closely at your background for the job, especially if he is gang involved as they will assume that you to are gang involved. Also of course assuming they approve you you would not be able to work at the facility where he is locked up.
Unless there was something HIGHLY UNUSUAL going on that would be a no. Observing a urine sample being given would normally be done by MEDICAL staff and not custody staff.
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