Anybody or case I've heard of doesn't get choices like that, although some of what you're talking about is what parole is for.
Sentence is 20 years. Eligible for parole in 10. If approved, serve the rest of the time out here under some set of conditions, sometimes fairly strict/limiting. Violate any of the conditions they get locked up again.
They do have the option of not applying for parole, sitting out all their time, and being "free" upon release.
Except they're really not free. Still can't vote, or own firearms. Some have to register and be on lists and aren't allowed to live certain places, etc.
I'm coming at it from the angle of, if the sentence is X, and they did X in whatever acceptable manner, they should be made whole again. Redemption has to play a part in this.
If they can't be trusted with all their rights and freedoms they should still be on parole or locked up, but if some representative(s) of "society", judge or jury, says this bad thing you did is worth X, and the person does X, they've upheld their end of the deal and should be given another shot at living truly free again, or as free as the rest of us do anyway.