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.
Hard to do this sort of thing by delayed-action remote control, but I will hazard a guess. He has an old case for possession which they chose to not prosecute for at the time but now, for some reason, they are prosecuting it. Maybe they have better info now and think it will stick. Maybe they want to keep him in custody for something totally unrelated to the charges and it is just a stalling tactic. It is completely kosher as long s they are within the statute of limitations. You and he are gonna have to roll with it unless you have a good lawyer.
As far as I know there is no LEGAL problem with a Correctional Officer getting involved with an ex-felon AS LONG AS THAT EX-FELON IS NO LONGER ON PROBATION OR PAROLE. Also of course you would, for practical purposes, have to let him know about your past. It would be a problem for access for firearms and ammunition, assuming he owns a gun. You are (presumably) prohibited from possessing or having access to guns or ammunition. Whether there would be some informal kickback against him, that is another question altogether.
Each system has its own rules about such things. As long as they are not actual relatives and you disclose the relationship I would be very much surprised if it would present any problem.
The California prisons I am familiar with did not have outside surveillance on a routine basis when I retired nearly 13 years ago. There is, however, no legal prohibition against doing so. Were I setting up such as thing I would do it on the entrance road(s), which are usually very defined and limited. You would get better utility for money spent that way.
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Not in California. Might in other jurisdictions. Also you would almost certainly NOT be able to work in whatever facility your fiancé is locked up in as that is an obvious security issue. If you fail to report the relationship and they find out about it later that could get you fired.
General speaking (IMHO) people gravitate to this line of work because they are process oriented, the structure appeals to them. Once in a while you get to do something that is THE RIGHT THING just because it is the right thing. During the time I ran the reception center I had three new arrivals tell me "This is a screw-up. I shouldn't be here." All of them were telling the truth. It would have gotten taken care of eventually but I got to fix it promptly because of the position I was in and because I choose to believe them at that point in the process. It wasn't all rainbows and sunshine, but it was nice.
As far as #1 I used to know the answer to that, at least in California, but I don't any more. I have been retired almost 13 years and I just don't remember. I THINK the answer is NO but I wouldn't bet on that. Your inheritance would have nothing to do with your son's status as a felon. He is free to inherit property and to leave property to others. Out of state transfer of prisoners are rare unless they have a case pending in the state they are transferred to. They are not unheard of, but they are rare.
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